HCID 23433565, compound → HCID 23433467, compound

HRID 1604786Notes

Reaction equation

HRID 1604786 reaction equation
[C:1]([O:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=1)=[O:8])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C.C(O)C>[C:1]([O:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[NH2:15])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 23433565HCID 23433565, compound

Product 1

HCID 23433467HCID 23433467, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To an oven-dried 1-L r.b. flask containing 1-tert-butyloxycarbamoyl-3-nitrobenzene (20.0 g, 83.9 mmol) in 500 mL 1:1 ethyl acetate/ethanol at rt was added 10% Pd on C (approx 1 mol %), and the mixture was stirred under an atmosphere of H2 gas for 6 h. The reaction mixture was then filtered, and concentrated under diminished pressure to give 17.4 g (quant of 3-tert-butyloxycarbamoylaniline as a white oily solid. Data for 3-tert-butyloxycarbamoylaniline: 1H NMR (400 MHz, CDCl3) 7.04 (t, J=8.0, 8.0, 1H, 5-H), 6.98 (br s, 1H, NH), 6.53 (dd, J=7.9, 1.8, 1H, 4-H), 6.36 (m, 2H, 6.2-H), 3.66 (br s, 2H, NH2), 1.51 [s, 9H, (CH3)3CO)].

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated under diminished pressure

Sources & evidence

ORD record
ord-e9981ea12e41443286c3fb997a1c13cc
Source dataset
uspto-grants-1999_11
Patent number
US05994544

Reaction notes

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