Hydrazine hydrate (1:1) → 1-(N-benzyl-tert.-butylamino)-3-(3-amino-2-hydroxy-phenoxy)-2-propanol

HRID 1105821Notes

Reaction equation

HRID 1105821 reaction equation
[CH2:1]([N:8]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:9][CH:10]([OH:23])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[C:14]=1[OH:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C.[Ni]>[CH2:1]([N:8]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:9][CH:10]([OH:23])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[C:14]=1[OH:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 570217691-(N-benzyl-tert.-butylamino)-3-(2-hydroxy-3-nitro-phenoxy)-2-propanol

Product 1

HCID 570867821-(N-benzyl-tert.-butylamino)-3-(3-amino-2-hydroxy-phenoxy)-2-propanol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 16.1 g of crude 1-(N-benzyl-tert.-butylamino)-3-(2-hydroxy-3-nitro-phenoxy)-2-propanol in 150 ml of ethanol is reduced, analogously to Example (4d), with 15 ml of hydrazine hydrate and Raney nickel to give 1-(N-benzyl-tert.-butylamino)-3-(3-amino-2-hydroxy-phenoxy)-2-propanol. The base forms a dark oil which is used further without further purification. The base crystallises from ether as greenish crystals with a melting point of 105°-110°.

Sources & evidence

ORD record
ord-3be6d86760fb4b8fb3de996614910711
Source dataset
uspto-grants-1982_01
Patent number
US04310527

Reaction notes

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