(Phenylmethyl)hydrazine → HCID 178515543, compound

HRID 1430608Notes

Reaction equation

HRID 1430608 reaction equation
[C:1]1([C:7]2[C:8](=[O:13])O[C:10](=[O:12])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([NH:21][NH2:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)(=O)C>[CH2:14]([N:21]1[C:10](=[O:12])[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([OH:13])=[N:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 11157(Phenylmethyl)hydrazineHCID 99174Phenylmaleic anhydride

Product 1

HCID 178515543HCID 178515543, compoundYield 344%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Phenylfuran-2,5-dione (2.00 g, 11.5 mmol), benzylhydrazine (3.36 g, 17.2 mmol) and acetic acid (2 mL) were heated to 140° C. for 3 h in a 20 mL heavy-walled sealed tube under microwave irradiation. Upon cooling, a white precipitate formed which was filtered and washed three times with hexane and DCM. The white solid was dried under reduced pressure to give the title compound (11.01 g). LCMS m/z=279.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 5.13 (s, 2H), 7.00 (s, 1H), 7.42-7.26 (m, 5H), 7.49-7.43 (m, 3H), 7.66-7.60 (m, 2H).

Workup

  1. temperatureUpon cooling
  2. customa white precipitate formed which
  3. filtrationwas filtered
  4. washwashed three times with hexane and DCM
  5. customThe white solid was dried under reduced pressure

Sources & evidence

ORD record
ord-13246bbbc7554359bad4991909468b75
Source dataset
uspto-grants-2015_01
Patent number
US08940891B2

Reaction notes

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