Dimethylformamide → 3-[1-(2-hydroxyethyl)-1H-indol-3-yl]-4-(1-methyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione

HRID 345693Notes

Reaction equation

HRID 345693 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[C:17](=[O:32])[O:18][C:19](=O)[C:20]=2[C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH3:30])[CH:22]=2)=[CH:8]1)(=O)C.C[N:34](C=O)C>N>[OH:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[C:17](=[O:32])[NH:34][C:19](=[O:18])[C:20]=2[C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH3:30])[CH:22]=2)=[CH:8]1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 151630463-[1-(2-Acetoxyethyl)-3-indolyl]-4-(1-methyl-3-indolyl)furan-2,5-dione

Product 1

HCID 53279283-[1-(2-hydroxyethyl)-1H-indol-3-yl]-4-(1-methyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of 1.6 g of 3-[1-(2-acetoxyethyl)-3-indolyl]-4-(1-methyl-3-indolyl)furan-2,5-dione in 4 ml of DMF and 8 ml of 33% aqueous ammonia was heated to 160° C. for 4 hours. The precipitate was filtered off and dried to give 1.04 g of 3-[1-(2-hydroxyethyl)-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, m.p. 250°-252° C.

Workup

  1. filtrationThe precipitate was filtered off
  2. customdried

Sources & evidence

ORD record
ord-5a3d081170634c44a6f14ec1ebc57770
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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