Water → Acemetacin

HRID 1659167

반응식

HRID 1659167 반응식
C(O[CH:5]([O:12][C:13](=[O:36])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]([C:26](=[O:34])[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[C:16]=1[CH3:35])C1C=CC=CC=1)(=O)C.[H][H].[OH2:39].CN(C)[CH:42]=[O:43]>[C].[Pd]>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([C:26]([N:17]2[C:18]3[C:23](=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:15]([CH2:14][C:13]([O:12][CH2:5][C:42]([OH:43])=[O:39])=[O:36])=[C:16]2[CH3:35])=[O:34])=[CH:28][CH:29]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 70621351[1-(p-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxy]-benzyl acetateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 1981Acemetacin

시약·촉매·용매 1

HCID 178418390HCID 178418390, 화합물촉매

실험 절차

50.6 g (0.1 mol) of [1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxy]-benzyl acetate were hydrogenated in 300 ml of absolute dimethylformamide in the presence of 5 g of 5% palladium carbon at 20°C within 15 minutes, with absorption of the calculated quantity of hydrogen. About 200 ml of water were added to the hydrogenation product, filtered through kieselguhr, until clouding started to occur and the solution was allowed to crystallise at 5°C. The crystallisate was suction-filtered, washed with water and dried under vacuum. The yield of [1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxy]-acetic acid amounted to 39 g which corresponds to 94% of the theoretical yield. The compound melted at 148°-149°C as determined on the Mettler melting point apparatus.

후처리

  1. filtrationfiltered through kieselguhr, until clouding
  2. customto crystallise at 5°C
  3. filtrationThe crystallisate was suction-filtered
  4. washwashed with water
  5. customdried under vacuum

출처 및 근거

ORD 기록
ord-774a4f600af94d9abcfd34aee544dbd8
출처 데이터셋
uspto-grants-1976_06
특허 번호
US03966956

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