Hydrazine hydrate (1:1) → Benzhydryl 2-aminooxyacetate

HRID 1200118Notes

Reaction equation

HRID 1200118 reaction equation
C1(=O)[N:5]([O:6][CH2:7][C:8]([O:10][CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])C(=O)C2=CC=CC=C12.O.NN>C(Cl)Cl.CO>[NH2:5][O:6][CH2:7][C:8]([O:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12784561Benzhydryl 2-phthalimidooxyacetate

Product 1

HCID 23358405Benzhydryl 2-aminooxyacetateYield 90.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl 2-phthalimidooxyacetate (10 g) in methylene chloride (100 ml) was added a solution of hydrazine hydrate (6.08 g) in methanol (7 ml). The reaction mixture was stirred at ambient temperature for an hour. The precipitates were collected by filtration and washed with methylene chloride. The filtrate and the washings were combined, adjusted to pH 7.0 with conc. hydrochloric acid, and washed with a saturated aqueous sodium chloride, and then dried over magnesium sulfate. The solution was evaporated in vacuo to give benzhydryl 2-aminooxyacetate (6.0 g).

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with methylene chloride
  3. washwashed with a saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-12c2e447967b4d618f8539136e2328d4
Source dataset
uspto-grants-1990_02
Patent number
US04904652

Reaction notes

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