Dichloromethane → Nicotinic Acid

HRID 21493

反応式

HRID 21493 の反応式
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

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 81531Diisopropylethylamine2 回HCID 122755Glycine methyl ester hydrochloride

生成物 1

HCID 938Nicotinic Acid

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9af7f773e9834ea6b09c56dfdf28ddd8
出典データセット
uspto-grants-1995_06
特許番号
US05424274

関連ノート

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