Acetic Acid → HCID 20380271, compound

HRID 1448570Notes

Reaction equation

HRID 1448570 reaction equation
O=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:5]2[C:14](=O)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:4]2=[C:3]1[C:22]#[N:23].[OH-].[K+].CC(C)([OH:29])C.C(O)(=O)C>O>[C:8]1([C:6]2[NH:7][CH2:2][C:3]([C:22]([NH2:23])=[O:29])=[C:4]3[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[CH2:14][C:5]=23)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 12669653HCID 12669653, compound

Product 1

HCID 20380271HCID 20380271, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1 part of 3,9-dihydro-3,9-dioxo-1-phenyl-2H-indeno[2,1-c]pyridine-4-carbonitrile, 5 parts of potassium hydroxide, and 39 parts of 1,1-dimethylethanol is heated at the boiling point under reflux for 16 hours. The resultant mixture is diluted with 1000 parts of water, followed by sufficient acetic acid to neutralize the base present. The precipitate which forms is filtered off; consecutively washed with water, methanol, and 1,1'-oxybisethane; and dried in vacuo. The resultant yellow solid is crystallized from aqueous N,N-dimethylformamide to afford 3,9-dihydro-1-phenyl-2H-indeno[2,1-c]pyridine-4-carboxamide melting above 300°. The product has the formula ##STR19##

Workup

  1. temperatureis heated at the boiling point
  2. temperatureunder reflux for 16 hours
  3. filtrationThe precipitate which forms is filtered off
  4. washconsecutively washed with water, methanol, and 1,1'-oxybisethane
  5. customand dried in vacuo
  6. customThe resultant yellow solid is crystallized from aqueous N,N-dimethylformamide

Sources & evidence

ORD record
ord-bf0756fa7efc4945ac465a32c1fa6888
Source dataset
uspto-grants-1979_12
Patent number
US04180666

Reaction notes

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