Methyl phenylacetate → Benzeneacetic acid, hydrazide

HRID 388271

Reaction equation

HRID 388271 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([CH:6](O)[C:7](O)=[O:8])=[CH:4][CH:3]=1.COC(=O)CC1C=CC=CC=1.O.[NH2:25][NH2:26]>C(O)C>[C:5]1([CH2:6][C:7]([NH:25][NH2:26])=[O:8])[CH:11]=[CH:12][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 7559Methyl phenylacetateHCID 24654Hydrazine hydrate (1:1)HCID 980684-Fluoromandelic acid2×

Product 1

HCID 70301Benzeneacetic acid, hydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The following representative compounds in Table 1 were synthesized according to (i) the foregoing procedures by selecting appropriate starting materials (for example, 4-fluoro mandelic acid derivatives (e.g., examples 12-1 and 12-3) were synthesized using commercially available 4-fluoromandelic acid) and (ii) known organic synthesis techniques (for example, treatment of commercially available α-phenylacetic acid methyl ester with hydrazine hydrate in ethanol under with heating provides phenyl-acetic acid hydrazide (see, e.g., Pandeye, S, N.; Manjula, H.; Stables, J. P.; Pharmazie; 2001, 56, 121-124) and treatment of phenyl acetic acid hydrazide with a substituted benzaldehyde in ethanol with heating and in the presence of catalytic acetic acid provides the corresponding substituted phenyl-acetic acid benzylidenehydrazide (see, e.g., Stephanidou-Stephanatou, J.; Lefkopoulou, S; Journal of Heterocyclic Chemistry; 1982; 19; 705-711.0)).

Workup

  1. customThe following representative compounds in Table 1 were synthesized
  2. customwere synthesized
  3. temperaturewith heating

Sources & evidence

ORD record
ord-dc6962bb739740efbb0c03a2685632cd
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Linked notes

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