Formaldehyde → HCID 23004024, compound

HRID 396353Notes

Reaction equation

HRID 396353 reaction equation
[CH2:1]([NH:8][CH2:9][CH:10]([C:12]1[C:21]2[C:16](=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:18]=[CH:19][CH:20]=2)[N:15]=[C:14]([C:26]([F:29])([F:28])[F:27])[CH:13]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30]=O>CO>[CH2:1]([N:8]1[CH2:9][CH:10]([C:12]2[C:21]3[C:16](=[C:17]([C:22]([F:23])([F:24])[F:25])[CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([C:26]([F:28])([F:29])[F:27])[CH:13]=2)[O:11][CH2:30]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 23004016HCID 23004016, compound

Product 1

HCID 23004024HCID 23004024, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of α-benzylaminomethyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol (142 mg, 0.34 mmol) in MeOH (3 mL) was added formaldehyde (0.2 mL, 37% in water), the mixture was refluxed for 30 mins, cooled, concentrated in vacuo, and the residue was suspended in heptane and filtered to give the title compound (41 mg, 28%) as a white solid: mp 108.5-108.9° C.; IR νmax (Nujol)/cm−1 2924, 2854, 1602, 1586, 1458, 1378, 1306, 1271, 1184, 1153, 1139, 1127, 1105, 775 and 726; NMR δH (400 MHz, CDCl3) 2.85 (1H, dd, J 11.7, 7.0 Hz), 3.77 (1H, dd, J 11.7, 7.4 Hz), 3.85 (1H, d, J 13.1 Hz), 3.90 (1H, d, 13.1 Hz), 4.71 (1H, d, J 5.8 Hz), 4.74 (1H, d, J 5.8 Hz), 5.72 (1H, t, J 7.0 Hz), 7.21-7.43 (5H, m), 7.72 (1H, t, J 7.9 Hz), 8.17 (1H, d, J 7.5 Hz), 8.11 (1H, s) and 8.03 (1H, d, J 8.1 Hz).

Workup

  1. temperaturethe mixture was refluxed for 30 mins
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered

Sources & evidence

ORD record
ord-279f8cafb4af4e22a6d32b726e6ff154
Source dataset
uspto-grants-2003_08
Patent number
US06608085B1

Reaction notes

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