Ethanol → HCID 66603345, compound

HRID 2263575Notes

Reaction equation

HRID 2263575 reaction equation
[Br:1][C:2]1C=[C:4]2[C:9](=[O:10])OC(=O)[C:5]2=[CH:11][CH:12]=1.[CH3:13][NH2:14].[CH3:15][CH2:16][OH:17]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:13][N:14]1[C:16](=[O:17])[C:15]2=[C:2]([Br:1])[CH:12]=[CH:11][CH:5]=[C:4]2[C:9]1=[O:10]

Participants

6

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 665904-Bromophthalic anhydride

Product 1

HCID 66603345HCID 66603345, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A solution of 4-bromophthalic anhydride (2.0 g) in toluene (20 mL) was treated with 33% methylamine in EtOH (1.65 mL) and a crystal of DMAP. After stirring for 1 h at ambient temperature, the mixture was heated to reflux under a dean-stark trap during 14 h. The reaction mixture was cooled to −20° C., and the resulting white crystals collected and washed with hexanes to give N-methyl-3-bromophthalimide (1.32 g) m.p. 149-151. Concentration of the mother liquor and recrystalization from benzene (3 mL) gave a second crop, 430 mg.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under a dean-stark trap during 14 h
  3. temperatureThe reaction mixture was cooled to −20° C.
  4. customthe resulting white crystals collected
  5. washwashed with hexanes

Sources & evidence

ORD record
ord-47112cecb1fc45898ba9ff57399f9813
Source dataset
uspto-grants-2010_12
Patent number
US07851637B2

Reaction notes

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