3,4-Dichlorobenzaldehyde → HCID 18353772, compound

HRID 430077Notes

Reaction equation

HRID 430077 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5](=[CH2:19])[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.[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH:24]=O.C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>>[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:24][NH:3][CH2:4][C:5](=[CH2:19])[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

5

Reactant 4

HCID 227103,4-DichlorobenzaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 18353696HCID 18353696, compound

Product 1

HCID 18353772HCID 18353772, compound

Procedure

The title compound was prepared according to the method described in Example 23(b) from 2-(2-aminomethylallylamino)-1H-quinolin-4-one dihydrochloride (85 mg, 0.28 mmol), 3,4-dichlorobenzaldehyde (50 mg, 0.29 mmol), sodium acetate (47 mg, 0.58 mmol) and sodium cyanoborohydride (18 mg, 0.29 mmol). The crude product was purified by silica gel chromatography eluting with dichloromethane and increasing concentrations of methanol containing 10% concentrated aqueous ammonia to yield a white solid. δH (CD3OD) 3.21(2H, s), 3.66(2H, s), 3.89(2H, s), 5.07(2H, d, J=8.41 Hz), 5.55(1H, s), 7.1-7.2(3H, m), 7.33(1H, d, J=8.2 Hz), 7.4-7.5(2H, m), 7.97(1H, d, J=8.75); MS (ES+) 388 (100%) MH+.

Workup

  1. customThe crude product was purified by silica gel chromatography
  2. washeluting with dichloromethane
  3. temperatureincreasing concentrations of methanol containing 10% concentrated aqueous ammonia
  4. customto yield a white solid

Sources & evidence

ORD record
ord-94e203fd43744d94a8554fd1e4b375a2
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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