Dichloromethane → Nicotinic Acid

HRID 21493

반응식

HRID 21493 반응식
Cl.C[O:3][C:4](=[O:7])[CH2:5]N.C([N:10]([CH:14](C)C)[CH:11]([CH3:13])C)C.[CH2:17](Cl)Cl>>[N:10]1[CH:11]=[CH:13][CH:17]=[C:5]([C:4]([OH:3])=[O:7])[CH:14]=1

참가 물질

4

반응물 3

HCID 6344DichloromethaneHCID 81531Diisopropylethylamine2회HCID 122755Glycine methyl ester hydrochloride

생성물 1

HCID 938Nicotinic Acid

실험 절차

The acid chloride starting material of Example 1 (12.81 g=0.0345 mole) was dissolved in 100 ml CH2Cl2. To this solution was added 4.68 g (0.0373 mol) of glycine methyl ester hydrochloride. This mixture was cooled in an ice bath before adding 10 ml of ethyldiisopropylamine (EDPA) (0.0574 mole) by pipet. The ice bath was removed, and the reaction stirred overnight at room temperature. 19F NMR showed the reaction was incomplete. An additional 3 ml of EDPA (0.172 mol) was added. After 1/2 hour a gas chromatographic assay showed complete reaction. It was washed with dilute HCl and extracted with CH2C2. The CH2Cl2 layer was dried with MgSO4, filtered and concentrated to 14.2 g orange oily solid. Two grams were chromatotroned (20% EtOAc/cyclohexane) and then recyrstallized to give 1.2 g of 3-pyridinecarboxylic acid, 6-(difluoromethyl)-5-[[(2-methoxy-2-oxoethyl)amino]carbonyl]-4-(2-methylpropyl)-2-(trifluoromethyl)-, methyl ester as a white solid. m.p. 126°-129° C.

후처리

  1. temperatureThis mixture was cooled in an ice bath
  2. customThe ice bath was removed
  3. waitAfter 1/2 hour a gas chromatographic assay showed complete
  4. customreaction
  5. washIt was washed with dilute HCl
  6. extractionextracted with CH2C2
  7. dry with materialThe CH2Cl2 layer was dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to 14.2 g orange oily solid

출처 및 근거

ORD 기록
ord-9af7f773e9834ea6b09c56dfdf28ddd8
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424274

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