Ammonia → HCID 23283703, compound

HRID 370059Notes

Reaction equation

HRID 370059 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][N:14]1[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]1=[O:21].Cl.N.CS(C)=[O:26]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:26])[CH:6]2[CH2:12][CH2:13][N:14]1[C:15](=[O:21])[CH2:16][CH2:17][CH2:18][C:19]1=[O:20]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 23283702HCID 23283702, compound

Product 1

HCID 23283703HCID 23283703, compound

Procedure

145 mg of N-[2-(5-methoxyindol-3-yl)ethyl]glutarimide are dissolved in DMSO (30 μl) in a round-bottomed flask and concentrated HCl (72 μl) is added with stirring. The mixture is stirred overnight at room temperature. The crude product is neutralized with NH3 and then extracted with EtOAc. After separation on a silica plate, N-[2-(5-methoxy-2-oxo-2,3-dihydroindol-3-yl)ethyl]glutarimide is obtained.

Workup

  1. stirringThe mixture is stirred overnight at room temperature
  2. extractionextracted with EtOAc
  3. customAfter separation on a silica plate

Sources & evidence

ORD record
ord-39ccf2a2f91c48b9a9ce7785531a9364
Source dataset
uspto-grants-2000_10
Patent number
US06140372

Reaction notes

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