4-Isopropoxycarbonylamino-2-nitroaniline → 1,2-Diamino-4-isopropoxycarbonylaminobenzene

HRID 2071797Notes

Reaction equation

HRID 2071797 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([NH:11][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.[H][H]>CO.[Pt]=O>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([NH:11][C:12]([O:14][CH:15]([CH3:16])[CH3:17])=[O:13])=[CH:10][C:4]=1[NH2:1]

Participants

5

Reactant 2

HCID 126780374-Isopropoxycarbonylamino-2-nitroanilineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 126780381,2-Diamino-4-isopropoxycarbonylaminobenzeneYield 66.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of a solution of 2-nitro-4-isopropoxycarbonylaminoaniline (17.9 g, 0.075 mole) in methanol (450 ml) and platinum oxide (1.0 g) was shaken in an atmosphere of hydrogen at atmospheric pressure and laboratory temperature for several hours, during which time 5.04 liters of hydrogen were absorbed. The mixture was filtered, and the methanol removed in vacuo and the dark solid residue recrystallised from benzene to give 1,2-diamino-4-isopropoxycarbonylaminobenzene (10.4 g), m.p. 108°-110° C.

Workup

  1. customwere absorbed
  2. filtrationThe mixture was filtered
  3. customthe methanol removed in vacuo
  4. customthe dark solid residue recrystallised from benzene

Sources & evidence

ORD record
ord-22ab45fac708435cae7f3fe6b69fef14
Source dataset
uspto-grants-1977_09
Patent number
US04048326

Reaction notes

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