Indacrinone → {1-Oxo-2-[4-(2-chloroacetamidomethyl)phenyl]-2-methyl-6,7-dichloro-5-indanyloxy}acetic acid

HRID 839703Notes

Reaction equation

HRID 839703 reaction equation
O[CH2:2][NH:3][C:4](=[O:7])[CH2:5][Cl:6].[O:8]=[C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:20][CH2:21][C:22]([OH:24])=[O:23])=[C:15]([Cl:19])[C:16]=2[Cl:18])[CH2:11][C:10]1([CH3:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>S(=O)(=O)(O)O.C(O)(=O)C>[O:8]=[C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:20][CH2:21][C:22]([OH:24])=[O:23])=[C:15]([Cl:19])[C:16]=2[Cl:18])[CH2:11][C:10]1([C:25]1[CH:30]=[CH:29][C:28]([CH2:2][NH:3][C:4](=[O:7])[CH2:5][Cl:6])=[CH:27][CH:26]=1)[CH3:31]

Participants

5

Reactant 2

HCID 42266IndacrinoneHCID 62466N-Methylol-alpha-chloroacetamide2×

Product 1

HCID 12423624{1-Oxo-2-[4-(2-chloroacetamidomethyl)phenyl]-2-methyl-6,7-dichloro-5-indanyloxy}acetic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

Well-pulverized N-hydroxymethyl-2-chloroacetamide (3.37 g., 0.0274 mole) is added portionwise to (1-oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetic acid (10.0 g., 0.0274 mole) in 36N sulfuric acid (100 ml.) and acetic acid (100 ml.) with stirring at 40°-50° C. over one-half hours. Additional N-hydroxymethyl-2-chloroacetamide (1.68 g., 0.014 mole) is added over a four hour period until no starting material remains. After stirring at 25° C. for 16 hours the reaction mixture is added to crushed ice-water (2 l.) to precipitate 11.9 g. of {1-oxo-2-[4-(2-chloroacetamidomethyl)phenyl]-2-methyl-6,7-dichloro-5-indanyloxy}acetic acid which melts at 138°-141° C. and is used in the next step without purification.

Workup

  1. stirringAfter stirring at 25° C. for 16 hours the reaction mixture
  2. additionis added
  3. customto precipitate 11.9 g
  4. customof {1-oxo-2-[4-(2-chloroacetamidomethyl)phenyl]-2-methyl-6,7-dichloro-5-indanyloxy}acetic acid which melts at 138°-141° C. and is used in the next step without purification

Sources & evidence

ORD record
ord-aa849edfd24e42cda9ae0a48b102039f
Source dataset
uspto-grants-1978_06
Patent number
US04096267

Reaction notes

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