Formic Acid → N-[4-(2-Chlorophenyl)-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-C]carbazol-9-YL]formamide

HRID 11164Notes

Reaction equation

HRID 11164 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.[CH:27](O)=[O: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][CH:27]=[O:28])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 219806569-Amino-4-(2-chlorophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 24778473N-[4-(2-Chlorophenyl)-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-C]carbazol-9-YL]formamideYield 54%

Procedure

Amine (919) prepared as described in example 467 and formic acid were reacted using the procedure described in example 468 with a reaction time of 4 h to give the formamide (921) (54%) as a yellow powder, mp 293–297° C. 1H NMR δ [(CD3)2SO] 12.11 (s, 0.5H), 12.08 (s, 1H), 11.12 (s, 0.5H), 11.08 (s, 1H), 10.34 (s, 1H), 10.30 (s, 0.5H), 9.03 (d, J=1.9 Hz, 1H), 8.69 (m, 0.5H), 8.31 (d, J=1.8 Hz, 1.5H) 7.92 (dd, J=8.8, 1.9 Hz, 1H) 7.42–7.65 (m, 9.5H). Found: C, 64.78; H, 3.53; N, 9.96. C21H12ClN3O3.1/4 THF requires: C, 64.86; H, 3.44; N, 10.32.

Workup

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

Sources & evidence

ORD record
ord-17b7dca0d68344b3a6052000b5c2298a
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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