Methanol → HCID 21105725, compound

HRID 1354362Notes

Reaction equation

HRID 1354362 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:30])[C:7]=1[NH:8][C:9]([C:11]1[C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([N+:24]([O-])=O)[CH:21]=3)[N:16]([CH3:27])[C:15]=2[C:14]([O:28][CH3:29])=[CH:13][CH:12]=1)=[O:10].CO>CN(C=O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:30])[C:7]=1[NH:8][C:9]([C:11]1[C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([NH2:24])[CH:21]=3)[N:16]([CH3:27])[C:15]=2[C:14]([O:28][CH3:29])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 887MethanolHCID 21105726HCID 21105726, compound

Product 1

HCID 21105725HCID 21105725, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

N-(3,5-dichloropyrid-4-yl)—1-methoxy-9-methyl-6-nitro-9H-4-carbazolecarboxamide (250 mg) was suspended in DMF (20 ml) and methanol (10 ml) and added with raney nickel (25 mg, 10% w/w) and reduced under pressure (60 psi) for 18 hrs at room temperature. The reaction mixture was filtered through celite and DMF was evaporated to get a green solid which was washed with water to give N-(3,5-dichloropyrid-4-yl)-1-methoxy-9-methyl-6-amino-9H-4-carbazolecarboxamide. Confirmed by ninhydrin. The compound was taken directly without purification to synthesize the following example no 54,55,56 and 57

Workup

  1. filtrationThe reaction mixture was filtered through celite and DMF
  2. customwas evaporated
  3. customto get a green solid which
  4. washwas washed with water

Sources & evidence

ORD record
ord-d6257f87a3654f2f94f5ad944b501a35
Source dataset
uspto-grants-2007_05
Patent number
US07223789B2

Reaction notes

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