Benzaldehyde → HCID 3772128, compound

HRID 648111Notes

Reaction equation

HRID 648111 reaction equation
[Cl-].[Cl-].[CH3:3][N:4](B)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CCCC)CCCC)CCC>C(Cl)Cl>[CH3:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 7622TributylamineHCID 178419229HCID 178419229, compound

Product 1

HCID 3772128HCID 3772128, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of N-methylanilinoborane dichloride (100 mg) in methylene chloride (5 ml), a solution of benzaldehyde (56 mg) and tri-n-butylamine (99 mg) in methylene chloride (2 ml) is added with ice cooling, and the resultant mixture is stirred at room temperature for 1 hour. The reaction mixture is mixed with ice pieces and shaken with methylene chloride. The methylene chloride layer is washed with aqueous sodium carbonate and a saturated brine in that order, and evaporated under reduced pressure to remove the solvent. The residue is chromatographed on a column of silica gel, and the product is recrystallized from chloroform-petroleum ether to give 2-methylaminobenzhydrol (85 mg) as crystals melting at 124° to 126° C. The yield is 75.0%.

Workup

  1. additionThe reaction mixture is mixed with ice pieces
  2. washThe methylene chloride layer is washed with aqueous sodium carbonate
  3. customa saturated brine in that order, and evaporated under reduced pressure
  4. customto remove the solvent
  5. customThe residue is chromatographed on a column of silica gel
  6. customthe product is recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-cb3e2eefe1b34f0c9780432fb033b36a
Source dataset
uspto-grants-1983_10
Patent number
US04410730

Reaction notes

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