Water → HCID 13069713, compound

HRID 27184Notes

Reaction equation

HRID 27184 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[C:11]([CH3:14])=[C:10]([CH3:15])[C:9]2=[O:16])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+].O>CO>[CH3:1][C:2]1[CH:3]=[C:4]([N:8]2[C:9](=[O:16])[C:10]([CH3:15])=[C:11]([CH3:14])[CH:12]2[OH:13])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 130698313,4-Dimethyl-1-(3-methylphenyl)-1H-pyrrole-2,5-dione

Product 1

HCID 13069713HCID 13069713, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 20 g (0.93 mole) of the resulting N-(3-methylphenyl)-dimethyl-maleimide in 180 ml of methanol is added at 20° 7.2 g (0.185 mole) of sodium borohydride in portions so small that the temperature does not exceed 40°. An intense evolution of gas is observed. The reaction mixture is initially a clear colourless solution, but soon becomes a white suspension, which is poured after one hour into water. The white substance which has precipitated out is filtered off, washed well with methanol and dried under reduced pressure to obtain 18.6 g of white crystals (92.1% of theory), which melt at 170°-172° (compound No. 9, Table I).

Workup

  1. customdoes not exceed 40°
  2. customThe white substance which has precipitated out
  3. filtrationis filtered off
  4. washwashed well with methanol
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-3fff823fcf614a8cba57b19eebddcbea
Source dataset
uspto-grants-1980_09
Patent number
US04220655

Reaction notes

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