Hydrochloric Acid → HCID 14209956, compound

HRID 1031438Notes

Reaction equation

HRID 1031438 reaction equation
COC1C=CC(C(Cl)=O)=CC=1.Cl.[CH3:13][C:14]1([CH3:39])[C:23]2[C:18](=[CH:19][C:20]([N+:35]([O-])=O)=[C:21]([NH:24][C:25](=O)[C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[CH:22]=2)[NH:17][C:16](=[O:38])[CH2:15]1.N1C2C(=CC=CC=2)CCC1=O>N1C=CC=CC=1>[CH3:13][C:14]1([CH3:39])[C:23]2[CH:22]=[C:21]3[NH:24][C:25]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)=[N:35][C:20]3=[CH:19][C:18]=2[NH:17][C:16](=[O:38])[CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 64796HydrocarbostyrilHCID 14209949HCID 14209949, compound

Product 1

HCID 14209956HCID 14209956, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.7 g. (20 mmole) of the above compound were mixed in 50 ml. pyridine, while cooling with ice, with 3.7 g. (22 mmole) 4-methoxybenzoyl chloride. After 2 hours at 25° C., the reaction mixture was poured on to ice, acidified with 2N hydrochloric acid, extracted with methylene chloride, dried and evaporated to give 6.9 g. (93% of theory) 4,4-dimethyl-6-(4-methoxybenzoylamino)-7-nitro-1,2,3,4-tetrahydroquinolin-2one; 1,2,3,4-tetrahydroquinolin-2-one; m.p. 288-290° C.

Workup

  1. additionthe reaction mixture was poured on to ice
  2. extractionextracted with methylene chloride
  3. customdried
  4. customevaporated
  5. customto give 6.9 g

Sources & evidence

ORD record
ord-c41cd0f4476948a3a078756b0f60bec7
Source dataset
uspto-grants-1990_09
Patent number
US04954498

Reaction notes

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