Dimethylformamide → HCID 19696329, compound

HRID 863687Notes

Reaction equation

HRID 863687 reaction equation
C([O:4][CH:5]1[CH2:34][N:9]2[C:10]3[C:15]([C:16]([C:17]4[C:18](=[O:33])[O:19][C:20](=O)[C:21]=4[C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24]([CH3:31])[CH:23]=4)=[C:8]2[CH2:7][CH2:6]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=O)C.C[N:36](C)C=O>N>[OH:4][CH:5]1[CH2:34][N:9]2[C:10]3[C:15]([C:16]([C:17]4[C:18](=[O:33])[NH:36][C:20](=[O:19])[C:21]=4[C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24]([CH3:31])[CH:23]=4)=[C:8]2[CH2:7][CH2:6]1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 19696432HCID 19696432, compound

Product 1

HCID 19696329HCID 19696329, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of 150 mg of 3-[7-acetoxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)furan-2,5-dione in 6 ml of dimethylformamide and 6 ml of 33% aqueous ammonia was heated to 150° C. for 6 hours. The mixture was extracted with ethyl acetate and the organic extracts were washed with water, dried and evaporated. Crystallization of the residue from ethyl acetate gave 120 mg of 3-[6,7,8,9-tetrahydro-7-hydroxypyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione of melting point 252°-255° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic extracts were washed with water
  3. customdried
  4. customevaporated
  5. customCrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-f0c8c74face34567891aced81872e44a
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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