Acetic Acid → n-[4-(2-Chlorophenyl)-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-9-yl]acetamide

HRID 11165Notes

Reaction equation

HRID 11165 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:7]4[C:22](=[O:26])[NH:23][C:24](=[O:25])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1.[C:27](O)(=[O:29])[CH3:28]>>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:8]1[C:7]2[C:22](=[O:26])[NH:23][C:24](=[O:25])[C:6]=2[C:5]2[C:4]3[CH:3]=[C:2]([NH:1][C:27](=[O:29])[CH3:28])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 219806569-Amino-4-(2-chlorophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 21980397n-[4-(2-Chlorophenyl)-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-9-yl]acetamideYield 43%

Procedure

Amine (919) prepared as described in example 467 and acetic acid were reacted using the procedure described in example 468 with a reaction time of 4 h to give the acetamide (926) (43%) as a yellow powder, mp 240–245° C. 1H NMR δ [(CD3)2SO] 12.04 (br s, 1H), 11.07 (br s, 1H), 10.10 (s, 1H), 8.95 (d, J=2.1 Hz, 1H), 7.90 (dd, J=8.8, 2.1 Hz, 1H), 7.58 (m, 2H), 7.42–7.51 (m, 4H), 2.10 (s, 3H). FABMS found: [M+H]+=404.0787, 406.0776. C22H15ClN3O3 requires 404.0802, 406.0772.

Workup

  1. customwere reacted
  2. customdescribed in example 468 with a reaction time of 4 h

Sources & evidence

ORD record
ord-4f9bd3b0dcd2418e9894710a2a8be279
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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