Isonicotinic Acid → HCID 178429213, compound

HRID 1088948Notes

Reaction equation

HRID 1088948 reaction equation
P(Cl)(Cl)(Cl)=[O:2].[NH2:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH3:18])([CH3:17])[C:12](=[O:16])[NH:13]2)=[CH:9][C:8]=1[N+:19]([O-])=O.CN(C)C=[O:25].[C:27](O)(=[O:34])[C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1>N1C=CC=CC=1>[OH2:2].[OH2:16].[OH2:25].[OH2:34].[CH3:17][C:11]1([CH3:18])[C:10]2[C:14](=[CH:15][C:7]3[NH:6][C:27]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)=[N:19][C:8]=3[CH:9]=2)[NH:13][C:12]1=[O:16]

Participants

6

Reactant 4

HCID 5922Isonicotinic AcidHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 13589235HCID 13589235, compound

Product 1

HCID 178429213HCID 178429213, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.15 ml. Phosphorus oxychloride are added to a solution of 221 mg. (1 mmol) 6-amino-5-nitro-3,3-dimethyl-indolin-2-one in 2 ml. dimethylformamide containing 0.5 ml. pyridine and 123 mg. (4 mmol) isonicotinic acid. The reaction mixture is then stirred for about 3 hours, poured on to ice water and the crystals obtained are filtered off with suction. Subsequently, the product is hydrogenated in 10 ml. ethanol containing 0.2 ml. triethylamine in the presence of Pd/C. The catalyst is then filtered off with suction, the filtrate is evaporated and the residue is heated under reflux for about 6 hours in a solution of 5 ml. ethanol and 1 ml. concentrated hydrochloric acid. The reaction mixture is then evaporated, digested with an aqueous solution of ammonia and the product obtained recrystallised from ethanol/water. Yield: 220 mg. (63% of theory); m.p. 215° C.

Workup

  1. customthe crystals obtained
  2. filtrationare filtered off with suction
  3. filtrationThe catalyst is then filtered off with suction
  4. customthe filtrate is evaporated
  5. temperaturethe residue is heated
  6. temperatureunder reflux for about 6 hours in a solution of 5 ml
  7. customThe reaction mixture is then evaporated
  8. customthe product obtained
  9. customrecrystallised from ethanol/water

Sources & evidence

ORD record
ord-3b2c4691d7024ada92e252b95eab3eeb
Source dataset
uspto-grants-1990_10
Patent number
US04963686

Reaction notes

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