Acetic Acid → METHYL 2-METHOXY-6-METHYLPYRIDINE-3-CARBOXYLATE

HRID 2177658ノート

反応式

HRID 2177658 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1Cl.[Na].[C:14](O)(=[O:16])C>CO.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1[O:16][CH3:14]

参加物

7

反応物 3

HCID 176Acetic AcidHCID 5360545Sodium2 回HCID 13055804Methyl 2-chloro-6-methylpyridine-3-carboxylate

生成物 1

HCID 10910170METHYL 2-METHOXY-6-METHYLPYRIDINE-3-CARBOXYLATE

試薬・触媒・溶媒 3

HCID 887Methanol溶媒3 回HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 2-chloro-6-methyl-nicotinic acid methyl ester (10.4 g, 56.52 mmol) in MeOH under nitrogen is added a solution of sodium (2.58 g, 113.04 mmol) in methanol (80.0 mL) (sodium metal is dissolved in methanol under a nitrogen atmosphere) at room temperature. The reaction mixture is refluxed overnight. The reaction is cooled to room temperature and the pH is adjusted to pH=7 with acetic acid. The reaction mixture is diluted with ethyl acetate (100 mL) and water (30 mL). The organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×75 mL). The combined organic extracts are dried over Na2SO4, filtered, and concentrated to give crude product. Yield: 7.25 g (71%). 1H NMR (400 MHz, CDCl3), δ8.066-8.047 (d, J=7.6 Hz, 1H), 6.782-6.764 (d, J=7.2 Hz, 1-1H), 4.029 (s, 3H), 3.879 (s, 3H), 2.483 (s, 3H); ES/MS m/z 182.2 [M+H]+.

後処理

  1. temperatureThe reaction mixture is refluxed overnight
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with ethyl acetate (2×75 mL)
  4. dry with materialThe combined organic extracts are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude product

出典と根拠

ORDレコード
ord-aaa03f6945f040bca35bd6002d079408
出典データセット
uspto-grants-2015_06
特許番号
US09067920B2

反応ノート

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