HCID 23433467, compound → HCID 22279055, compound

HRID 850349Notes

Reaction equation

HRID 850349 reaction equation
[C:1]([O:5][NH:6][C:7]([C:9]1[C:14]([CH3:15])=[C:13]([N+:16]([O-])=O)[CH:12]=[CH:11][CH:10]=1)=[O:8])([CH3:4])([CH3:3])[CH3:2].C(ONC(C1C=C(C=CC=1)N)=O)(C)(C)C>>[NH2:16][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([C:7](=[O:8])[NH:6][O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:14]=1[CH3:15]

Participants

3

Reactant 2

HCID 23433467HCID 23433467, compoundHCID 23433515HCID 23433515, compound

Product 1

HCID 22279055HCID 22279055, compoundYield 99%

Procedure

This compound was prepared from 6-tert-butyloxycarbamoyl-2-nitrotoluene (4.60 g, 18.2 mmol) in a manner similar to that described for 3-tert-butyloxycarbamoylaniline (EXAMPLE 13), affording 4.00 g (99%) of the desired aniline as a colorless oil. Data for 2-amino-6-tert-butyloxycarbamoyltoluene: 1H NMR (400 MHz, CDCl3) 7.04 and 6.81 (br δ of ABq, 2H, JAB =8.0 Hz, JA =0 Hz, JB =7.9 Hz, 4,5-H), 6.49 (d, 1H, J=8.3 Hz, 3-H), 6.26 (br s, 1H, NH), 3.61 (br s, 2H, NH2), 2.02 (s, 3H, 1-CH3), 1.51 [s, 9H, (CH3)3CO)].

Sources & evidence

ORD record
ord-a404d6aaf1d24f82b1c1f3b6abd08501
Source dataset
uspto-grants-2000_01
Patent number
US06017924

Reaction notes

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