Ammonia → 3-(8-(Hydroxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione

HRID 863665Notes

Reaction equation

HRID 863665 reaction equation
C(OCC1C[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]2C1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=O)C.[NH3:36]>CN(C)C=O>[OH:19][CH2:18][CH:17]1[CH2:21][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[CH2:16]1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

4

Reactant 2

HCID 222AmmoniaHCID 103898823-[8-(Acetoxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)furan-2,5-dione

Product 1

HCID 103876943-(8-(Hydroxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.90 g of 3-[8-(acetoxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)furan-2,5-dione in 30 ml of dimethylformamide and 23 ml of 33% aqueous ammonia was heated to 140° C. for 7 hours. The mixture was extracted with ethyl acetate and the combined organic extracts were washed with water, dried over anhydrous sodium sulfate and evaporated to dryness. Crystallization of the residue from ethyl acetate gave 1.87 g of 3-[6,7,8,9-tetrahydro-8-(hydroxymethyl)pyrido-[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione in the form of a red solid of melting point 262°-263° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe combined organic extracts were washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness
  5. customCrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-f0cb4aa9fa0d4adca14af8a811a6c694
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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