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Chemical Structure| 5470-70-2

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Product Details of Methyl 6-methylnicotinate

CAS No. :5470-70-2
Formula : C8H9NO2
M.W : 151.16
SMILES Code : O=C(OC)C1=CN=C(C)C=C1
MDL No. :MFCD00006340
InChI Key :VYPPZXZHYDSBSJ-UHFFFAOYSA-N
Pubchem ID :231548

Safety of Methyl 6-methylnicotinate

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

Application In Synthesis of Methyl 6-methylnicotinate

* 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.

  • Upstream synthesis route of [ 5470-70-2 ]
  • Downstream synthetic route of [ 5470-70-2 ]

[ 5470-70-2 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 5470-70-2 ]
  • [ 19733-96-1 ]
References: [1] Patent: EP2417973, 2012, A1, .
[2] Patent: US2012/122914, 2012, A1, .
  • 2
  • [ 5470-70-2 ]
  • [ 16188-55-9 ]
  • [ 221615-72-1 ]
YieldReaction ConditionsOperation in experiment
72% With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1 h; To the reaction flask was added llg (4-methylthio) phenylacetic acid,200 mL of anhydrous THF, and the mixture was heated to 65-70 ° C.Maintain T = 65-70 ° C while dropping175 Mll. 0 M t-BuMgCl in THF and5.7g6-methylpyridine-3-carboxylate50 ml of THF solution. Dropping to complete the incubation reaction for 1 hour.Cooling to room temperature, dropping 50ml4M hydrochloric acid quenching reaction, stratification, organic layer and then 50ml4M hydrochloric acid extraction,The aqueous layer was added and the aqueous layer was added with 50 g of sodium hydroxide,Heated to 40-50 ° C for 3 hours, cooled to room temperature,Filtration gave 6.9 g of a pale yellow solid, 72.0percent yield, 97.3percent pure
References: [1] Patent: CN104045596, 2017, B, . Location in patent: Paragraph 0040-0042.
[2] Patent: CN108689917, 2018, A, . Location in patent: Paragraph 0036; 0044-0050; 0056-0061.
  • 3
  • [ 5470-70-2 ]
  • [ 221615-72-1 ]
YieldReaction ConditionsOperation in experiment
87.7% With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1 h; To the reaction flask was added llg (4-methylthio) phenylacetate, 200 mL of anhydrous THF, and the mixture was heated to 65-70The (: Maintaining T = 65-70 ° C while adding 88 ml of a solution of 1.0 M t-BuMgCl in THF and 5.7 g of 6-methylpyridine-3-carboxylic acid methylEster in 50 ml of THF. Dropping to complete the incubation reaction for 1 hour. Cooled to room temperature, dropping 50 ml of 4 M hydrochloric acid, layered, organic layerAnd then 50ml of 4M hydrochloric acid extraction, the water layer, the water layer by adding 50g sodium hydroxide, heated to 40-50 ° C stirring 3 hours, cooling toAt room temperature and filtered to give 8.3 g of a pale yellow solid, 87.7percent yield, 98.6percent pure
References: [1] Patent: CN104045596, 2017, B, . Location in patent: Paragraph 0045-0046.
  • 4
  • [ 5470-70-2 ]
  • [ 221615-72-1 ]
YieldReaction ConditionsOperation in experiment
78.5% With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1 h; To the reaction flask was added llg (4-methylthio) phenylacetate, 200 mL of anhydrous THF, and the mixture was heated to 65-70 The (: Maintaining T = 65-70 ° C while adding 88 ml of a solution of 1.0 M t-BuMgCl in THF and 5.7 g of 6-methylpyridine-3-carboxylic acid methyl Ester in 50 ml of THF. Dropping to complete the incubation reaction for 1 hour. Cooled to room temperature, dropping 50 ml of 4 M hydrochloric acid, layered, organic layer And then 50ml of 4M hydrochloric acid extraction, the water layer, the water layer by adding 50g sodium hydroxide, heated to 40-50 ° C stirring 3 hours, cooling to At room temperature and filtered to give 7.4 g of a pale yellow solid, yield 78.5percent, purity 98.1
References: [1] Patent: CN104045596, 2017, B, . Location in patent: Paragraph 0043-0044.
  • 5
  • [ 5470-70-2 ]
  • [ 38746-92-8 ]
  • [ 221615-72-1 ]
References: [1] Patent: US2013/245272, 2013, A1, . Location in patent: Paragraph 0099.
  • 6
  • [ 5470-70-2 ]
  • [ 221615-72-1 ]
References: [1] Journal of Organic Chemistry, 2000, vol. 65, # 25, p. 8415 - 8420.
[2] Patent: WO2012/66570, 2012, A2, .
[3] Patent: US2013/245272, 2013, A1, .
[4] Patent: CN103664754, 2016, B, .
[5] Patent: CN103664754, 2016, B, .
 

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