Tetrahydrofuran → tert-butyl N-(5-amino-2-methoxyphenyl)carbamate

HRID 583924Notes

Reaction equation

HRID 583924 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C1COCC1>[Pd].CO>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:5]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 45790233Tert-butyl 2-methoxy-5-nitrophenylcarbamate

Product 1

HCID 22344747tert-butyl N-(5-amino-2-methoxyphenyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 28A in 1:1 THF:methanol (40 mL) was treated with 10% palladium on carbon (800 mg), stirred under hydrogen (1 atm) for one hour, filtered through diatomaceous earth (Celite®), and concentrated to provide the desired product.

Workup

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-56f5141ec05b47fb838a30fba23b5338
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Reaction notes

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