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

HRID 2177658노트

반응식

HRID 2177658 반응식
[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]

참가 물질

7

반응물 3

HCID 176Acetic AcidHCID 5360545Sodium2회HCID 13055804Methyl 2-chloro-6-methylpyridine-3-carboxylate

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매3회HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-aaa03f6945f040bca35bd6002d079408
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067920B2

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