N-Methylaniline → N-methyl-N,2-diphenylquinoline-4-carboxamide

HRID 986282Notes

Reaction equation

HRID 986282 reaction equation
Cl.[C:2]1([C:8]2[CH:17]=[C:16]([C:18](Cl)=[O:19])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH3:21][N:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:17]=1)=[O:19]

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 123740002-Phenylquinoline-4-carbonyl chloride hydrochloride

Product 1

HCID 946063N-methyl-N,2-diphenylquinoline-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Phenylquinoline-4-carboxylic acid chloride hydrochloride (10.7 g) is added in portions over a period of 15 minutes, with stirring, to a solution of N-methylaniline (12.8 g) in methylene chloride (75 ml), cooled to 0° C. The mixture is stirred for 2 hours 30 minutes at 10° C. The solution obtained is washed with a 20% strength solution of acetic acid in water (120 ml). The acetic acid solution is extracted with methylene chloride (100 ml). The organic phases are combined, washed with water (3×100 ml), dried over magnesium sulphate and evaporated under reduced pressure.

Workup

  1. customThe solution obtained
  2. washis washed with a 20% strength solution of acetic acid in water (120 ml)
  3. extractionThe acetic acid solution is extracted with methylene chloride (100 ml)
  4. washwashed with water (3×100 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-79e966aa3b0246f9bb51dc1041f024ee
Source dataset
uspto-grants-1987_12
Patent number
US04711890

Reaction notes

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