Acetic Acid → Indacrinone

HRID 839699Notes

Reaction equation

HRID 839699 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13]CC#N)=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([CH3:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24]([OH:27])(=[O:26])[CH3:25].S(=O)(=O)(O)O>O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:25][C:24]([OH:27])=[O:26])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([CH3:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 12423629(1-Oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetonitrile

Product 1

HCID 42266Indacrinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (1-oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetonitrile (3.0 g.), Example 19, Step A, acetic acid (20 ml.), water (5 ml.) and concentrated sulfuric acid (5 ml.) is refluxed for 2 hours then poured into ice-water (100 ml.) affording 2.5 g. of (1-oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 168°-169° C. after recrystallization from acetic acid.

Workup

  1. temperatureis refluxed for 2 hours
  2. customaffording 2.5 g
  3. customof (1-oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 168°-169° C. after recrystallization from acetic acid

Sources & evidence

ORD record
ord-2aaad639afc4481597fb70347165a0f1
Source dataset
uspto-grants-1978_06
Patent number
US04096267

Reaction notes

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