Methyl 4-nitrobutyrate → HCID 717394, compound

HRID 1941488Notes

Reaction equation

HRID 1941488 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C[O:11][C:12](=O)[CH2:13][CH2:14][CH2:15][N+:16]([O-:18])=[O:17].C([O-])(=O)C.[NH4+:24]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C@@H:5]2[NH:24][C:12](=[O:11])[CH2:13][CH2:14][C@H:15]2[N+:16]([O-:18])=[O:17])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 25604Methyl 4-nitrobutyrateHCID 765833-BromobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 717394HCID 717394, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-bromobenzaldehyde (82.20 g), methyl-4-nitrobutyrate (65.3 g) and ammonium acetate (68.5 g) in ethanol (400 ml), was heated to reflux for 18 hours. The solvent was removed in vacuo and the resultant mixture triturated with ethanol (400 ml) to give the title compound as a white solid (97.46 g). NMR (CDCl3) δ 2.30 (1H, m), 2.55 (3H, m), 4.70 (1H, m), 5.25 (1H, m), 6.7 (1H, s), 7.2-7.6 (4H, m).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. customThe solvent was removed in vacuo
  4. customthe resultant mixture triturated with ethanol (400 ml)

Sources & evidence

ORD record
ord-77254a06e3c64affbc2efc7e4e0860ab
Source dataset
uspto-grants-1997_12
Patent number
US05703240

Reaction notes

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