Hydrazine hydrate (1:1) → HCID 54519375, compound

HRID 1603843Notes

Reaction equation

HRID 1603843 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[C:19]=1[NH:27][CH3:28])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.NN>[Pd].C(O)C>[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[C:19]=1[NH:27][CH3:28])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54321793HCID 54321793, compound

Product 1

HCID 54519375HCID 54519375, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a mixture of N-benzyl-[2-(2-methylamino-3-nitro-phenoxy)-ethyl]-carbamic acid tert-butyl ester (520 mg, 1.30 mmol) and 10% palladium on carbon (120 mg) in ethanol (40 mL) at 50° C. was added a solution of hydrazine hydrate (1.3 g) in ethanol (10 mL). The reaction was allowed to stir for 3 hr then the catalyst filtered through celite and the solvent removed. Purification by chromatography (30% ethyl acetate-hexane) afforded 380 mg (78.9%) of a clear oil; MS EI m/e 371 (M+); IR (film) 3400, 3350, 1680 cm-1.

Workup

  1. filtrationthe catalyst filtered through celite
  2. customthe solvent removed
  3. customPurification by chromatography (30% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-f236ca6994234caf987129adea53a76b
Source dataset
uspto-grants-1999_11
Patent number
US05990144

Reaction notes

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