3,4-Dichlorobenzaldehyde → 2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-1H-quinolin-4-one hydrochloride

HRID 430060Notes

Reaction equation

HRID 430060 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[NH:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH:21]=O.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[ClH:17].[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:21][NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[NH:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

6

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 108569252-[(3-Aminopropyl)amino]-1,4-dihydroquinolin-4-one

Product 1

HCID 98229982-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-1H-quinolin-4-one hydrochlorideYield 115.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent3×

Procedure

To a solution of 2-(3-aminoprop-1-ylamino)-1H-quinolin-4-one (0.477 g, 2.2 mmol) in methanol (20 ml) and acetic acid (0.5 ml) was added 3,4-dichlorobenzaldehyde (0.385 g, 2.2 mmol) in methanol (5 ml). After stirring under argon for 30 min, sodium cyanoborohydride (0.207 g, 3.3 mmol) in methanol (3 ml) was added and the reaction stirred for 2 h. The reaction mixture was then cooled in an ice bath, and the precipitate filtered off, washed with cold methanol then dichloromethane and dried in vacuo to give the title compound as a pink powder (0.526 g, 64%); δH (CD3OD/DCl) 2.1-22.5 (2H, m), 3.2-3.4 (2H, m, under methanol), 3.62-3.73 (2H, m), 4.27 (2H, s), 6.38 (1H, s), 7.4-7.95 (6H, m), 8.1(1H, d); MS (ES+) 376, 378 (50, 33%, MH+) and 201 (100).

Workup

  1. stirringthe reaction stirred for 2 h
  2. temperatureThe reaction mixture was then cooled in an ice bath
  3. filtrationthe precipitate filtered off
  4. washwashed with cold methanol
  5. dry with materialdichloromethane and dried in vacuo

Sources & evidence

ORD record
ord-41f5be622f334e38a517816d22424de4
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

Loading…