84228-43-3|Ethyl 3-amino-4-nitrobenzoate| Ambeed

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Quality Control of [ 84228-43-3 ] Purity: 98% SDS Specification

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Product Details of [ 84228-43-3 ]

CAS No. :	84228-43-3
Formula :	C₉H₁₀N₂O₄
M.W :	210.19
SMILES Code :	O=C(OCC)C1=CC=C([N+]([O-])=O)C(N)=C1
MDL No. :	MFCD14584886
InChI Key :	ANNPFRZKDGTZHX-UHFFFAOYSA-N
Pubchem ID :	13170941

Safety of [ 84228-43-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 84228-43-3 ]

* 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 [ 84228-43-3 ]

[ 84228-43-3 ] Synthesis Path-Downstream 1~22

1
[ 64-17-5 ]
[ 6968-22-5 ]
[ 84228-43-3 ]

References: [1]Chemische Berichte,1885,vol. 18,p. 2942.

2
[ 84228-43-3 ]
[ 131508-15-1 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1891,vol. <2> 43,p. 464.

3
[ 84228-43-3 ]
[ 37466-90-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium/active carbon; In methanol; at 50℃; for 16h;	Five-percent palladium on carbon (0.50 g) was added to a solution of 4.00 g of ethyl 3-amino-4-nitro-benzoate in 100 ml of methanol, and the mixture was stirred in a hydrogen atmosphere at 50 C. for 16 hours.. The solid material was separated through filtration, and the filtrate was concentrated to obtain ethyl 3,4-diaminobenzoate..

References: [1]Patent: US6352985,2002,B1 .Location in patent: Page column 83.

4
[ 75-03-6 ]
silver salt of/the/ 4-nitro-3-amino-benzoic acid [ No CAS ]
[ 84228-43-3 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1891,vol. <2> 43,p. 464.

5
[ 587-48-4 ]
[ 84228-43-3 ]

References: [1]Chemische Berichte,1885,vol. 18,p. 2942.

6
[ 54002-27-6 ]
[ 84228-43-3 ]

References: [1]Chemische Berichte,1885,vol. 18,p. 2942.

7
[ 84228-43-3 ]
[ 75-36-5 ]
[ 193013-89-7 ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; ethyl acetate; N,N-dimethyl-aniline;	PRODUCTION EXAMPLE 12 Production of ethyl 3-acetylamino-4-nitrobenzoate Nine milliliters of acetyl chloride were added to a mixture of 18.4 g of <strong>[84228-43-3]ethyl 3-amino-4-nitrobenzoate</strong> and 200 ml of N,N-dimethylaniline while being cooled with ice. The mixture was stirred at room temperature for 2 hours and then at 50 C. for 2 hours. The reaction solution was poured into cold 1-N hydrochloric acid, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with 1-N hydrochloric acid and then with water, and was dried. The solvent was then distilled off under reduced pressure. The residue was purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and hexane at a ratio of from 1:10 to 1:4) to give 19.6 g of ethyl 3-acetylamino-4-nitrobenzoate. Properties of the compound: 1 H-NMR(CDCl3, δ): 1.42(3H, t, J=7.1 Hz), 2.32(3H, s), 4.43(2H, q, J=7.1 Hz), 7.82(1H, dd, J=1.8 and 8.7 Hz), 8.25(1H, d, J=8.7 Hz), 9.35(1H, d, J=1.8 Hz), 10.19(1H, s).
	In N,N-dimethylaniline; at 0 - 50℃; for 4h;	Nine milliliters of acetyl chloride were added to a mixture of 18.4 g of <strong>[84228-43-3]ethyl 3-amino-4-nitrobenzoate</strong> and 200 ml of N,N-dimethylaniline while being cooled with ice.. The mixture was stirred at room temperature for 2 hours and then at 50 C. for 2 hours.. The reaction solution was poured into cold 1-N hydrochloric acid, and the mixture was extracted twice with ethyl acetate.. The organic layer was washed with 1-N hydrochloric acid and then with water, and was dried.. The solvent was then distilled off under reduced pressure.. The residue was purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and hexane at a ratio of from 1:10 to 1:4) to give 19.6 g of ethyl 3-acetylamino-4-nitrobenzoate. Properties of the compound: 1H-NMR(CDCl3, δ): 1.42(3H, t, J=7.1 Hz), 2.32(3H, s), 4.43(2H, q, J=7.1 Hz), 7.82(1H, dd, J=1.8 and 8.7 Hz), 8.25(1H, d, J=8.7 Hz), 9.35(1H, d, J=1.8 Hz), 10.19(1H, s).

References: [1]Patent: US6166219,2000,A .
[2]Patent: US6352985,2002,B1 .Location in patent: Page column 58.

8
[ 38870-89-2 ]
[ 84228-43-3 ]
[ 193014-23-2 ]

Yield	Reaction Conditions	Operation in experiment
		PRODUCTION EXAMPLE 45 Production of ethyl 3-methoxyacetylamino-4-nitrobenzoate Ethyl 3-methoxyacetylamino-4-nitrobenzoate (18.7 g) was obtained from 15.0 g of <strong>[84228-43-3]ethyl 3-amino-4-nitrobenzoate</strong> and 15.0 g of methoxyacetyl chloride in the same manner as in Production Example 12. Properties of the compound: 1 H-NMR(CDCl3, δ): 1.42(3H, t, J=7.2 Hz), 3.58(3H, s), 4.11(2H, s), 4.43(2H, q, J=7.2 Hz), 7.85(1H, dd, J=1.6 and 8.7 Hz), 8.27(1H, d, J=8.7 Hz), 9.44(1H, d, J=1.6 Hz), 11.15(1H, s).
		Ethyl 3-methoxyacetylamino-4-nitrobenzoate (18.7 g) was obtained from 15.0 g of <strong>[84228-43-3]ethyl 3-amino-4-nitrobenzoate</strong> and 15.0 g of methoxyacetyl chloride in the same manner as in Production Example 12. Properties of the compound: 1H-NMR(CDCl3, δ): 1.42(3H, t, J=7.2 Hz), 3.58(3H, s), 4.11(2H, s), 4.43(2H, q, J=7.2 Hz), 7.85(1H, dd, J=1.6 and 8.7 Hz), 8.27(1H, d, J=8.7 Hz), 9.44(1H, d, J=1.6 Hz), 11.15(1H, s)

References: [1]Patent: US6166219,2000,A .
[2]Patent: US6352985,2002,B1 .Location in patent: Page column 125.

9
[ 84228-43-3 ]
[ 103-80-0 ]
ethyl 4-nitro-3-phenylacetylaminobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		PRODUCTION EXAMPLE 13 Production of ethyl 4-nitro-3-phenylacetylaminobenzoate In the same manner as in Production Example 12, 3.30 g of ethyl 4-nitro-3-phenylacetylaminobenzoate were formed from 2.02 g of <strong>[84228-43-3]ethyl 3-amino-4-nitrobenzoate</strong> and 1.87 g of phenylacetyl chloride. Properties of the compound: 1 H-NMR(CDCl3, δ): 1.41(3H, t, J=7.2 Hz), 3.85(2H, s), 4.42(2H, q, J=7.2 Hz), 7.34-7.49(5H, m), 7.79(1H, m), 8.19(1H, d, J=8.7 Hz), 9.39(1H, d, J=1.6 Hz), 10.15(1H, s).
		In the same manner as in Production Example 12, 3.30 g of ethyl 4-nitro-3-phenylacetylaminobenzoate were formed from 2.02 g of <strong>[84228-43-3]ethyl 3-amino-4-nitrobenzoate</strong> and 1.87 g of phenylacetyl chloride. Properties of the compound: 1H-NMR(CDCl3, δ): 1.41(3H, t, J=7.2 Hz), 3.85(2H, s), 4.42(2H, q, J=7.2 Hz), 7.34-7.49(5H, m), 7.79(1H, m), 8.19(1H, d, J=8.7 Hz), 9.39(1H, d, J=1.6 Hz), 10.15(1H, s).

References: [1]Patent: US6166219,2000,A .
[2]Patent: US6352985,2002,B1 .Location in patent: Page column 58.

10
[ 6968-22-5 ]
[ 18107-18-1 ]
[ 84228-43-3 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; hexane; dichloromethane; at 20℃;	(Trimethylsilyl)diazomethane (6mL, 2M solution in hexanes) was added to a solution of 3-amino-4-nitro-benzoic acid in CH2CI2 (25 mL) and methanol (25 mL). Stirred at room temperature until bubbling ceased. Concentrated under vacuum to provide 1.2g of desired product. MS (DCI) m/e 197 (M+H)+.

References: [1]Patent: WO2004/76424,2004,A1 .Location in patent: Page 268.

11
[ 84228-43-3 ]
[ 89457-09-0 ]