Formaldehyde → HCID 59859905, compound

HRID 1944523Notes

Reaction equation

HRID 1944523 reaction equation
[CH2:1]([NH:9][C:10]1[CH:28]=[CH:27][C:13]([C:14]([NH:16][C:17]2[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:15])=[CH:12][CH:11]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C=O.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>ClCCCl>[CH3:31][N:9]([CH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:10]1[CH:28]=[CH:27][C:13]([C:14]([NH:16][C:17]2[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:15])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 59859907HCID 59859907, compound

Product 1

HCID 59859905HCID 59859905, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-phenethylamino-N-quinolin-3-yl-benzamide (0.213 g, 0.57 mmol), paraformaldehyde (0.17 g, 5.8 mmol) and tetramethylammonium triacetoxyborohydride (0.37 g, 1.42 mmol) in 1,2-dichloroethane (˜10 mL) was heated at reflux for 6 hours. The resultant solution was washed with saturated aqueous sodium bicarbonate and applied to a flash silica gel column. The product was eluted with ethyl acetate (40%) in hexanes to give the product, 0.2 g (92%). MS: m/z 382 (MH+). 1H NMR (DMSO-d6): 2.90 (t, 2 H), 2.93 (s, 3 H), 3.66 (t, 2 H), 6.73 (d, 2 H), 7.21-7.35 (m, 5 H), 7.53 (d of t, 1 H), 7.63 (d of t, 1 H), 7.80-7.87 (m, 3 H), 8.05 (m, 1 H), 8.85 (d, 1H) and 8.91 (d, 1 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. washThe resultant solution was washed with saturated aqueous sodium bicarbonate
  4. washThe product was eluted with ethyl acetate (40%) in hexanes
  5. customto give the product, 0.2 g (92%)

Sources & evidence

ORD record
ord-c891a969af5745039de6e496adf2dd0b
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

Loading…