4-[alpha-(2,4-Ditert.-pentylphenoxy)-butyroyl]-6-benzyloxy-7-nitro-1,4-benzoxazine-3-one → 4-[alpha-(2,4-Ditert.-pentylphenoxy)-butyroyl]6-hydroxy-7-amino-1,4-benzoxazine-3-one

HRID 34704Notes

Reaction equation

HRID 34704 reaction equation
[C:1]([C:6]1[CH:39]=[C:38]([C:40]([CH2:43][CH3:44])([CH3:42])[CH3:41])[CH:37]=[CH:36][C:7]=1[O:8][CH:9]([CH2:34][CH3:35])[C:10]([N:12]1[C:17]2[CH:18]=[C:19]([O:25]CC3C=CC=CC=3)[C:20]([N+:22]([O-])=O)=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:33])=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2].[H][H]>C1COCC1.[Pd]>[C:1]([C:6]1[CH:39]=[C:38]([C:40]([CH2:43][CH3:44])([CH3:41])[CH3:42])[CH:37]=[CH:36][C:7]=1[O:8][CH:9]([CH2:34][CH3:35])[C:10]([N:12]1[C:17]2[CH:18]=[C:19]([OH:25])[C:20]([NH2:22])=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:33])=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 212986804-[alpha-(2,4-Ditert.-pentylphenoxy)-butyroyl]-6-benzyloxy-7-nitro-1,4-benzoxazine-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 212986754-[alpha-(2,4-Ditert.-pentylphenoxy)-butyroyl]6-hydroxy-7-amino-1,4-benzoxazine-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The nitro compound ((f), 8.19 g, 0.0136 mole) in THF (ml 100) was reduced and debenzylated under 25 PSI hydrogen pressure at room temperature in the presence of 10% Pd on charcoal. The resulting amine (g) was not isolated.

Sources & evidence

ORD record
ord-ea4052d7a95f44e4b5f1ed5285bed7eb
Source dataset
uspto-grants-1988_08
Patent number
US04762925

Reaction notes

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