Formaldehyde → HCID 18791387, compound

HRID 1005582Notes

Reaction equation

HRID 1005582 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][C:13]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:14]=2[NH2:15])=[CH:7][CH:6]=1)=[O:4].C=O.[C:23]([BH3-])#N>CO.C(O)(=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][O:12][C:13]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:14]=2[NH:15][CH3:23])=[CH:9][CH:10]=1)=[O:4]

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 498716Cyano-borohydrideHCID 18791559HCID 18791559, compound

Product 1

HCID 18791387HCID 18791387, compoundYield 80.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(4-methoxycarbonylphenyl)methoxy-4-methylaniline (420 mg) and 37% formaldeyde solution (69.7 mg) in a mixture of methanol (10 ml) and actic acid (0.1 ml) was added soduim cyanoborohydride (146 mg) and the mixture was stirred at amibient temperature for 3 hours. The solution was diluted with ethyl acetate (30 ml) and washed successively with saturated aqueous sodium hydrogen carbonate, water and brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was purified by silica gel column (chloroform) to give 2-(4-methoxycarbonylphenyl)methoxy-4-methyl-N-methylaniline (356 mg).

Workup

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate, water and brine
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by silica gel column (chloroform)

Sources & evidence

ORD record
ord-55f32bf5537d4e75b577e6ebb3f4e361
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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