Aniline → HCID 23338158, compound

HRID 903327Notes

Reaction equation

HRID 903327 reaction equation
Cl.Cl[CH:3]1[C:12]2[NH:11][C:10](=[O:13])[CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)(C)C>[NH:14]([CH:3]1[C:12]2[NH:11][C:10](=[O:13])[CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 23454280HCID 23454280, compound

Product 1

HCID 23338158HCID 23338158, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

110 g (0.5 mol) of 8-chloro-5,6,7,8-tetrahydro-2-quinolone hydrochloride are suspended in 800 ml of isopropanol and at 80° C. 186 g (2.0 mols) of aniline are added dropwise. A clear solution gradually forms which is refluxed for 10 minutes. The colorless crystalline 8-aniline-5,6,7,8-tetrahydro-2-quinolone separating on cooling is filtered off with suction and washed with acetonitrile. It is obtained in a yield of 94 g, corresponding to 78.3% of the theory and melts at 225° C.

Workup

  1. temperatureis refluxed for 10 minutes
  2. filtrationis filtered off with suction
  3. washwashed with acetonitrile
  4. customIt is obtained in a yield of 94 g, corresponding to 78.3% of the theory and melts at 225° C.

Sources & evidence

ORD record
ord-bf1b04a34ea442508ad2747ffb57e4f9
Source dataset
uspto-grants-1980_10
Patent number
US04226997

Reaction notes

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