HCID 59745240, compound → HCID 24990432, compound

HRID 2196868Notes

Reaction equation

HRID 2196868 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-a800dcfa11024baf9cd6ceacf018d564
Source dataset
uspto-grants-2012_12
Patent number
US08338487B2

Reaction notes

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