Maleic Anhydride → HCID 14473344, compound

HRID 2308822Notes

Reaction equation

HRID 2308822 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[C:8]1(=[O:14])[O:13][C:11](=[O:12])[CH:10]=[CH:9]1>C(Cl)Cl>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][C:8](=[O:14])/[CH:9]=[CH:10]\[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 14473344HCID 14473344, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aminoacetaldehyde dimethyl acetal (90 g, 0.857 mol) was added over 45 min to a 16° C. mixture of 84 g (0.857 mol) of purified maleic anhydride (azeotropic removal of H2O by distillation of xylene from crude anhydride) in 855 mL of CH2Cl2 (reaction temperature below 30° C.). After 1 h all of the amine had reacted and the solvent was removed on a rotary evaporator to yield a yellow solid. Recrystallization from MeOH gave 138 g (75% yield) of white solid, mp 91°-92° C. Further recrystallization (toluene/MeOH) gave mp 93°-94.5° C.

Workup

  1. customthe solvent was removed on a rotary evaporator
  2. customto yield a yellow solid
  3. customRecrystallization from MeOH

Sources & evidence

ORD record
ord-87d03ecf6caa40529a153ac5ee1c9b71
Source dataset
uspto-grants-1987_09
Patent number
US04691026

Reaction notes

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