Acetic Acid → 2,3-diphenyl-1H-indole-5-carboxylic Acid

HRID 1392199Notes

Reaction equation

HRID 1392199 reaction equation
[C:1]1([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)N.C(O)(=O)C.Cl>O>[C:1]1([C:7]2[NH:16][C:18]3[C:26]([C:9]=2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 99482-PhenylacetophenoneHCID 120894-Hydrazinobenzoic acid

Product 1

HCID 39003082,3-diphenyl-1H-indole-5-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.96 g (10 mmol) of deoxybenzoin and 1.52 g of 4-hydrazinobenzoic acid were ground in a mortar and then fused in an open flask at 160° C. for 15 minutes (min). The cooled melt was admixed with 100 ml of acetic acid and 30 ml of concentrated hydrochloric acid and heated under reflux for 3 hours (h). The cooled solution was admixed with water, resulting in the precipitation of the product 2,3-diphenyl-1H-indole-5-carboxylic acid. The product was filtered off with suction and the residue was washed with water and dried. For purification, the crude product was stirred with warm toluene, filtered off with suction and dried again. This gave 2,3-diphenyl-1H-indole-5-carboxylic acid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours (h)

Sources & evidence

ORD record
ord-247662469629456b9020fdcff16643b5
Source dataset
uspto-grants-2008_03
Patent number
US07342029B2

Reaction notes

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