Methane → HCID 14677305, compound

HRID 1165802Notes

Reaction equation

HRID 1165802 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:22]2[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=2[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH:11]=1)([O-])=O.C>CN(C)C=O.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:22]2[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=2[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH:11]=1

Participants

5

Reactant 2

HCID 297MethaneHCID 11291264HCID 11291264, compound

Product 1

HCID 14677305HCID 14677305, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

0.5 g (1.51 mmole) 1,2,3,6-tetrahydro-4-(2-nitrophenyl)-1,3-dioxopyrrolo[3,4-c]carbazole (Example 2g) in 30 ml dimethylformamide are hydrogenated at room temperature with 0.27 g palladium on active charcoal (10%). After 4 hours, the catalyst is filtered off and the solution evaporated in a vacuum. The residue is stirred up with ethyl acetate, the crystals filtered off, and recrystallized from methanol. One obtains 4-(2-aminophenyl)-1,2,3,6-tetrahydro-1,3-dioxopyrrolo[3,4-c]carbazole in the form of yellow crystals of the mp >300° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe solution evaporated in a vacuum
  3. filtrationthe crystals filtered off
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-643a97937ad04fcaa83a1b3061407efa
Source dataset
uspto-grants-1990_03
Patent number
US04912107

Reaction notes

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