1074-87-9|(1H-Indol-7-yl)methanol| Ambeed

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Quality Control of [ 1074-87-9 ] Purity: 98% SDS Specification

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Product Details of [ 1074-87-9 ]

CAS No. :	1074-87-9
Formula :	C₉H₉NO
M.W :	147.17
SMILES Code :	OCC1=CC=CC2=C1NC=C2
MDL No. :	MFCD02179597
InChI Key :	UBJBKRMNBMMMHZ-UHFFFAOYSA-N
Pubchem ID :	2773460

Safety of [ 1074-87-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1074-87-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1074-87-9 ]

[ 1074-87-9 ] Synthesis Path-Downstream 1~27

1
[ 1074-87-9 ]
[ 1074-88-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	With manganese(IV) oxide; In dichloromethane; at 20℃; for 72.0h;	To a solution of the alcohol, <strong>[1074-87-9](1H-indol-7-yl)-methanol</strong> (8.0 g, 54.3 mmol) in 400 mL of methylene chloride was added activated manganese (IV) oxide (85%, 41.0 g, 0.40 mol), and stirred at ambient temperature for 72 h. After additional of 200 mL of methylene chloride and 400 mL of methanol to the reaction mixture, the whole mixture was filtered through a pad of silica gel to remove solid materials. The filtrate was concentrated to afford a crude product, which was purified by a column chromatography on silica gel to yield 1H-indole-7-carbaldehyde, I-1 (6.55 g, 83%). 1H-NMR (CDCl3).
83%		Example 17; Preparation of Al3; Indole-7 carboxyldehyde (K-44); Methyl 7-indolecarboxylate was prepared according to literature procedure {Batcho B. and Leimgruber, K., Org. Syn. VoI HV, page 34-40). To a solution of methyl 7-indolecarboxylate (13 g, 74.2 mmol) in anhydrous THF (250 niL) was added LiAlH4 (10.9 g, 0.288 mol) in portions, and reaction mixture was heated to reflux for 2h. After cooling to room temperature, the excess hydride was quenched by addition of water (12mL), 15% NaOH (12mL) and water (26mL). The solids were removed by filtration through a pad of Celite and filtrate was evaporated in vacuo to yield (lH-indol-7-yl)- methanol (10.7 g, 98%). 1HNMR (CDCl3). To a solution of the alcohol, (IH- indol-7-yl)-methanol (8.0 g, 54.3 mmol) in 400 mL of methylene chloride was added activated manganese (IV) oxide (85%, 41.0 g, 0.40 mol), and stirred at ambient temperature for 72h. After additional of 200 mL of methylene chloride and 400 mL of methanol to the reaction mixture, the whole mixture was filtered through a pad of silica gel to remove solid materials. The filtrate was concentrated to afford a crude product, which was purified by a column chromatography on silica gel to yield lH-indole-7-carbaldehyde, K-44 (6.55 g, 83%).
	In ethyl acetate n-hexane; dichloromethane;	iv) 7-Indolecarboxaldehyde Solid pyridinium dichromate (1.77 g, 5.1 mmol) was added in portions over 3 hours to a stirred solution of <strong>[1074-87-9]7-indolemethanol</strong> (0.5 g, 3.4 mmol) in dichloromethane (50 ml). The mixture was stirred for a further 2 hours then filtered through a pad of Celite filter aid. The filtrate was evaporated and the residue purified by chromatography on silica in ethyl acetate-hexane (1:3).

	In ethyl acetate n-hexane; dichloromethane;	Part D Preparation of 7-Indolecarboxaldehyde Solid pyridinium dichromate (1.77 g, 5.1 mmol) is added in portions over 3 hours to a stirred solution of <strong>[1074-87-9]7-indolemethanol</strong> (0.5 g, 3.4 mmol) in dichloromethane (50 ml). The mixture is stirred for a further 2 hours then filtered through a pad of Celite filter aid. The filtrate is evaporated and the residue purified by chromatography on silica in ethyl acetate-hexane (1:3).
	In ethyl acetate n-hexane; dichloromethane;	iv) 7-Indolecarboxaldehyde Solid pyridinium dichromate (1.77 g, 5.1 mmol) was added in prtions over 3 hours to a stirred solution of <strong>[1074-87-9]7-indolemethanol</strong> (0.5 g, 3.4 mmol) in dichloromethane (50 ml). The mixture was stirred for a furthe 2 hours then filtered through a pad of Celite filter aid. The filtrate was evaporated and the residue purified by chromatography on silica in ethyl acetatehexane (1:3).

References: [1]Synthetic Communications,2006,vol. 36,p. 1051 - 1056.
[2]Patent: US2006/79520,2006,A1 .Location in patent: Page/Page column 43.
[3]Patent: WO2006/44415,2006,A2 .Location in patent: Page/Page column 78; 106-107.
[4]Journal of the American Chemical Society,2006,vol. 128,p. 4023 - 4034.
[5]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4116 - 4125.
[6]Journal of the Chemical Society. Chemical communications,1985,p. 1172 - 1173.
[7]Patent: US5281593,1994,A .
[8]Patent: US5486612,1996,A .
[9]Patent: EP469833,1992,A1 .

2
[ 25128-35-2 ]
[ 1074-87-9 ]

References: [1]Journal of the Chemical Society. Chemical communications,1985,p. 1172 - 1173.

3
[ 93247-78-0 ]
[ 1074-87-9 ]

Yield	Reaction Conditions	Operation in experiment
98%		Example 1 Preparation of P001 Indole-7 carboxyldehyde (I-1). Ethyl Indole-7 m carboxylate was prepared according to literature procedure {Batcho B. and Leimgruber, K., Org. Syn. Vol IIV, page 34-40). To a solution of methyl 7-indolecarboxylate (13 g, 74.2 mmol) in 250 ml of anhydrous THF was added LiAlH4 (10.9 g, 0.288 mol) in portions, and reaction mixture was heated to reflux for 2 h. After cooling to room temperature, the excess hydride was quenched by addition of water (12 mL), 15percent NaOH (12 mL) and water (26 mL). The solids were removed by filtration through a pad of Celite and filtrate was evaporated in vacuo to yield (1H-indol-7-yl)-methanol (10.7 g, 98percent). 1H-NMR (CDCl3).
98%		Example 17; Preparation of Al3; Indole-7 carboxyldehyde (K-44); Methyl 7-indolecarboxylate was prepared according to literature procedure {Batcho B. and Leimgruber, K., Org. Syn. VoI HV, page 34-40). To a solution of methyl 7-indolecarboxylate (13 g, 74.2 mmol) in anhydrous THF (250 niL) was added LiAlH4 (10.9 g, 0.288 mol) in portions, and reaction mixture was heated to reflux for 2h. After cooling to room temperature, the excess hydride was quenched by addition of water (12mL), 15percent NaOH (12mL) and water (26mL). The solids were removed by filtration through a pad of Celite and filtrate was evaporated in vacuo to yield (lH-indol-7-yl)- methanol (10.7 g, 98percent). 1HNMR (CDCl3). To a solution of the alcohol, (IH- indol-7-yl)-methanol (8.0 g, 54.3 mmol) in 400 mL of methylene chloride was added activated manganese (IV) oxide (85percent, 41.0 g, 0.40 mol), and stirred at ambient temperature for 72h. After additional of 200 mL of methylene chloride and 400 mL of methanol to the reaction mixture, the whole mixture was filtered through a pad of silica gel to remove solid materials. The filtrate was concentrated to afford a crude product, which was purified by a column chromatography on silica gel to yield lH-indole-7-carbaldehyde, K-44 (6.55 g, 83percent).
	With acetic acid; In tetrahydrofuran; ethyl acetate n-hexane;	iii) 7-Indole methanol Solid lithium aluminum hydride (1.0 g) was added in portions over 1 hour to a stirred solution of methyl 7-indolecarboxylate (6.7 g) in tetrahydrofuran (100 ml). The mixture was stirred for a further 2 hours then excess lithium aluminium hydride was destroyed by addition of acetic acid, the mixture was diluted with aqueous sodium hydroxide and extracted with ethyl acetate. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:9 to 1:2) to give the product.

	With acetic acid; In tetrahydrofuran; ethyl acetate n-hexane;	Part C Preparation of 7-Indole Methanol Solid lithium aluminum hydride (1.0 g) is added in portions over 1 hour to a stirred solution of methyl 7-indolecarboxylate (6.7 g) in tetrahydrofuran (100 ml). The mixture was stirred for a further 2 hours then excess lithium aluminum hydride was destroyed by addition of acetic acid, the mixture is diluted with aqueous sodium hydroxide and extracted with ethyl acetate. The extract is dried and evaporated and the residue is chromatographed on silica in ethyl acetate-hexane (1:9 to 1:2) to give the product.
	With acetic acid; In tetrahydrofuran; ethyl acetate n-hexane;	iii) 7-Indole methanol Solid lithium aluminium hydride (10 g) was added in portions over 1 hour to a stirred solution of methyl 7-indole-carboxylate (6.7 g) in tetrahydrofuran (100 ml). The mixture was stirred for a further 2 hours then excess lithium aluminium hydride was destroyed by addition of acetic acid, the mixture was diluted with aqueous sodium hydroxide and extracted with ethyl acetate. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:9 to 1:2) to give the product.

References: [1]Patent: US2006/79520,2006,A1 .Location in patent: Page/Page column 43.
[2]Patent: WO2006/44415,2006,A2 .Location in patent: Page/Page column 78; 106-107.
[3]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4116 - 4125.
[4]Patent: US5281593,1994,A .
[5]Patent: US5486612,1996,A .
[6]Patent: EP469833,1992,A1 .

5
[ 886841-17-4 ]
[ 1074-87-9 ]

References: [1]Synthetic Communications,2006,vol. 36,p. 1051 - 1056.

6
[2-Nitro-3-((E)-2-pyrrolidin-1-yl-vinyl)-phenyl]-methanol [ No CAS ]
[ 1074-87-9 ]

References: [1]Synthetic Communications,2006,vol. 36,p. 1051 - 1056.

7
[ 1026131-79-2 ]
[ 1074-87-9 ]

References: [1]Synthetic Communications,2006,vol. 36,p. 1051 - 1056.

8
[ 1074-87-9 ]
C₂₈H₃₆N₂O₃S [ No CAS ]