Water → Acemetacin

HRID 1659167

Reaction equation

HRID 1659167 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 1981Acemetacin

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-774a4f600af94d9abcfd34aee544dbd8
Source dataset
uspto-grants-1976_06
Patent number
US03966956

Linked notes

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