Methanol → HCID 21105725, compound

HRID 131595Notes

Reaction equation

HRID 131595 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-d9db4e64e65f4c0babfb4c37acaff8fc
Source dataset
uspto-grants-2008_06
Patent number
US07384962B2

Reaction notes

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