Hydrochloric Acid → HCID 10071893, compound

HRID 863705Notes

Reaction equation

HRID 863705 reaction equation
C([O:4][CH2:5][CH2:6][CH:7]1[CH2:36][N:11]2[C:12]3[C:17]([C:18]([C:19]4[C:20](=[O:35])[O:21][C:22](=O)[C:23]=4[C:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]([CH3:33])[CH:25]=4)=[C:10]2[CH2:9][CH2:8]1)=[CH:16][CH:15]=[CH:14][CH:13]=3)(=O)C.[OH-].[Na+].Cl.C[N:41](C)C=O>N>[OH:4][CH2:5][CH2:6][CH:7]1[CH2:36][N:11]2[C:12]3[C:17]([C:18]([C:19]4[C:20](=[O:35])[NH:41][C:22](=[O:21])[C:23]=4[C:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]([CH3:33])[CH:25]=4)=[C:10]2[CH2:9][CH2:8]1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 10367979HCID 10367979, compound

Product 1

HCID 10071893HCID 10071893, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of 200 mg of 3-[7-(2-acetoxyethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-furan-2,5-dione in 2 ml of dimethylformamide and 1 ml of 33% aqueous ammonia was heated to 140° C. Then, 1 ml of a 2M solution of sodium hydroxide was added to the cooled solution and the mixture was stirred for 2 hours. The mixture was acidified with 2M hydrochloric acid and evaporated. The residue was partitioned between ethyl acetate and water and the organic phase was dried. The solvent was evaporated and the solid obtained was triturated with ethyl acetate to give 115 mg of 3-[6,7,8,9-tetrahydro-7-(2-hydroxyethyl)pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione of melting point 236°-238° C.

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe organic phase was dried
  4. customThe solvent was evaporated
  5. customthe solid obtained
  6. customwas triturated with ethyl acetate

Sources & evidence

ORD record
ord-91cec745d7bd4b6d95a47af449c5031c
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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