Formaldehyde → HCID 18353752, compound

HRID 430069Notes

Reaction equation

HRID 430069 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]1[NH:12][C:13]2[C:18]([C:19](=[O:21])[CH:20]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.[C:26]([BH3-])#N.[Na+].C=O>CO.C(O)(=O)C>[NH3:6].[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][N:6]([CH2:7][CH2:8][CH2:9][NH:10][C:11]1[NH:12][C:13]2[C:18]([C:19](=[O:21])[CH:20]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:26]

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 9822999HCID 9822999, compound

Product 2

HCID 222AmmoniaHCID 18353752HCID 18353752, compoundYield 197.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-1H-quinolin-4-one (0.026 g, 0.07 mmol) was dissolved in methanol (2 ml) and acetic acid (0.05 ml). This was cooled in an ice bath and treated sequentially with sodium cyanoborohydride (6.3 mg, 0.1 mmol) in methanol (0.4 ml) and formaldehyde (3.7% in water/methanol, 0.057 ml, 0.07 mmol) then stirred for 4 h. The reaction mixture was purified by chromatography on a SCX cartridge, eluting with methanol and then 0.2M NH3 in methanol to give the title compound as a pale pink solid (0.027 g, 99%); δH (CD3OD) 1.7-1.9 (2H, m), 2.16 (3H, s), 2.43 (2H, t), 3.25-3.35 (2H, m), 3.43 (2H, s), 5.57 (1H, s), 7.1-7.6 (6H, m), and 8.03 (1H, d); MS (ES+) 390, 392 (45, 30%, MH+) and 201 (100).

Workup

  1. temperatureThis was cooled in an ice bath
  2. customThe reaction mixture was purified by chromatography on a SCX cartridge
  3. washeluting with methanol

Sources & evidence

ORD record
ord-0c86ef7537ef49a1aac9604198c9e070
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

Loading…