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

HRID 430085Notes

Reaction equation

HRID 430085 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH:5]([O:19][CH3:20])[CH2:6][NH:7][C:8]1[CH2:17][C:16](=[O:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.C([O-])(=O)C.[Na+].[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH:30]=O.C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[NH3:3].[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:30][NH:3][CH2:4][CH:5]([O:19][CH3:20])[CH2:6][NH:7][C:8]1[NH:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

8

Reactant 4

HCID 227103,4-DichlorobenzaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 178495961HCID 178495961, compound

Product 2

HCID 222AmmoniaHCID 161289412-[3-(3,4-Dichlorobenzylamino)-2-methoxyprop-1-ylamino]-1H-quinolin-4-oneYield 48.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

A suspension of 2-(3-amino-2-methoxyprop-1-ylamino)quinolin-4-one dihydrochloride (0.15 g, 0.468 mmol), sodium acetate (0.096 g, 1.17 mmol) and 3,4-dichlorobenzaldehyde (0.082 g, 0.468 mmol) in 1% acetic acid in methanol (1.4 ml) was stirred at room temperature for 4 h. Sodium cyanoborohydride (0.059 g, 0.937mol) in methanol (1.1 ml) was added and stirring continued for 72 h. The mixture was concentrated and chromatographed (2%, 5% then 10% (10% 880 aqueous ammonia in methanol) in dichloromethane) to yield the title compound as a white solid (0.046 g, 24%). δH (CD3OD) 2.60-3.51 (5H, m, 2CH2CH, CHOCH3), 3.34 (3H, s, CHOCH3), 3.68-3.69 (2H, d, CH2Ar), 5.58 (1H, s, 3-H), 7.21-8.09 (7H, m, ArH). MS (ES+) 406 (M+).

Workup

  1. stirringstirring
  2. waitcontinued for 72 h
  3. concentrationThe mixture was concentrated
  4. customchromatographed (2%, 5%

Sources & evidence

ORD record
ord-47194069041040cea7321f3bcfe381bb
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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