Hydrazine hydrate (1:1) → 2-Hydrazino-2-oxo-N-(3-phenoxypropyl)acetamide

HRID 1713802Notes

Reaction equation

HRID 1713802 reaction equation
O.[NH2:2][NH2:3].[O:4]=[C:5]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6](OC)=[O:7]>C(O)C>[NH:2]([C:6](=[O:7])[C:5]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:4])[NH2:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68683629HCID 68683629, compound

Product 1

HCID 594643142-Hydrazino-2-oxo-N-(3-phenoxypropyl)acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Hydrazine monohydrate (6.3 mL) was added to a stirred suspension of methyl oxo[(3-phenoxypropyl)amino]acetate (3080 mg) in ethanol (50 mL). The reaction mixture was heated to 85° C. for 3 hours then allowed to cool. The precipitate was filtered off, washed with Et2O and dried under vacuum, to give the title compound (Intermediate 46, 2.269 g) as a solid; 1H NMR δ 9.95 (1H, s), 8.77 (1H, s), 7.28 (2H, m), 6.92 (3H, m), 4.50 (2H, s), 3.99 (2H, t), 3.30 (2H+H2O, m), 1.94 (2H, t); MS m/e MNa+ 260.

Workup

  1. temperatureto cool
  2. filtrationThe precipitate was filtered off
  3. washwashed with Et2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4979e409798c41f5bb03011af45e0b64
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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