Formaldehyde → HCID 20327931, compound

HRID 435941Notes

Reaction equation

HRID 435941 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C=O.[C:22]1(=O)NC(=O)C2=CC=CC=C12>C(O)C.[Ni]>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][CH3:22])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 6809PhthalimideHCID 18621725HCID 18621725, compound

Product 1

HCID 20327931HCID 20327931, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of α-t-butoxycarbonylamino-p-aminophenylacetic acid (26.6 g, 0.1 mol), formaldehyde (8.1 ml of a 37% aq. solution) and phthalimide (14.7 g, 0.1 mol) in 200 ml of absolute ethanol is heated at reflux for 1 hour. After cooling to room temperature Raney nickel catalyst is added and the mixture is hydrogenated under 60 psi of H2 100° for 2 hours. The catalyst is filtered off and the solvent is evaporated in vacuo. Following chromatography on silica gel the desired product is obtained.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. additionis added
  4. filtrationThe catalyst is filtered off
  5. customthe solvent is evaporated in vacuo
  6. customis obtained

Sources & evidence

ORD record
ord-5f26733eb7f7432780f26891d7b3de45
Source dataset
uspto-grants-1977_02
Patent number
US04007173

Reaction notes

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