Hydrazine hydrate (1:1) → 2371-31-5

HRID 2061406

Reaction equation

HRID 2061406 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12]CC)=O)=[CH:4][CH:3]=1.O.[NH2:16][NH2:17]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([NH:16][NH2:17])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 302644Glycine, N-(4-chlorophenyl)-, ethyl ester

Product 1

HCID 3026472371-31-5Yield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(4-chlorophenylamino)acetate (A) (25.6 g, 120 mmol) and hydrazine monohydrate (7.0 mL, 144 mmol) were heated to reflux in ethanol (120 mL) for 22 hours. After concentration in vacuo, the solid obtained was recrystallised from ethanol to yield the title compound (14.0 g, 59%) as a pale brown powder. 1H NMR (400 MHz, CDCl3) δ 3.85 (2H, d), 4.18 (2H, br), 6.53 (2H, d), 7.16 (2H, d), 7.60 (1H, br).

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe solid obtained
  3. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-4de39e719876495c897ec661c521281c
Source dataset
uspto-grants-2012_10
Patent number
US08283351B2

Linked notes

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