HCID 59745240, compound → HCID 24990432, compound

HRID 2422835Notes

Reaction equation

HRID 2422835 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[NH:5][C:6]1[CH:15]=[CH:14][C:13]2[CH:12]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH2:11][CH2:10][CH2:9][C:8]=2[C:7]=1[N+:27]([O-])=O)[CH3:2].C(OC(=O)NC1C([N+]([O-])=O)=CC2C(NC3C=CC(C(F)(F)F)=CC=3)CCCC=2C=1)C>CO.[Ni]>[CH2:1]([O:3][C:4](=[O:30])[NH:5][C:6]1[CH:15]=[CH:14][C:13]2[CH:12]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][CH:18]=3)[CH2:11][CH2:10][CH2:9][C:8]=2[C:7]=1[NH2:27])[CH3:2]

Participants

5

Reactant 2

HCID 59745240HCID 59745240, compoundHCID 59745245HCID 59745245, compound

Product 1

HCID 24990432HCID 24990432, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of a mixture of [1-nitro-5-(4-trifluoromethyl-phenylamino)-5,6,7,8-tetrahydro-naphthalen-2-yl]-carbamic acid ethyl ester and [3-Nitro-5-(4-trifluoromethyl-phenylamino)-5,6,7,8-tetrahydro-naphthalen-2-yl]-carbamic acid ethyl ester (500 mg) in 20 ml of methanol was added a catalytic amount of Raney Ni. The resulting mixture was hydrogenated under regular pressure at room temperature for 4 hours. The reaction mixture was filtered through celite and washed with methanol. The filtrate was evaporated to dryness in vacuo and the residue was separated by preparative HPLC to give two products as white solids in a quantitative yield.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with methanol
  3. customThe filtrate was evaporated to dryness in vacuo
  4. customthe residue was separated by preparative HPLC
  5. customto give two products as white solids in a quantitative yield

Sources & evidence

ORD record
ord-709577e62aed430a952ec3b4a6c66fe9
Source dataset
uspto-grants-2011_06
Patent number
US07960436B2

Reaction notes

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