Hydrogen Bromide → 4-(2-Aminoethyl)-7-hydroxyindolin-2-one hydrobromide

HRID 1446967Notes

Reaction equation

HRID 1446967 reaction equation
[BrH:1].Br.[NH2:3][CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]2[C:7]=1[CH2:8][C:9](=[O:17])[NH:10]2>>[BrH:1].[NH2:3][CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:7]=1[CH2:8][C:9](=[O:17])[NH:10]2

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 204812784-(2-aminoethyl)-7-methoxy-2(3H)-indolone hydrobromide

Product 1

HCID 128075524-(2-Aminoethyl)-7-hydroxyindolin-2-one hydrobromideYield 83%

Procedure

A 10 ml portion of constant boiling hydrobromic acid (48%) was dissolved from stannous chloride directly into the reaction vessel. To this was added 0.533 g (1.76 mmole) of 4-(2-aminoethyl)-7-methoxy-2(3H)-indolone hydrobromide and the reaction was stirred at reflux under argon for 3 hours then allowed to cool to room temperature. After being stored at 0° overnight, the reaction mixture was filtered. The solid was washed with cold methanol to give 0.40 g (83%) of 4-(2-aminoethyl)-7-hydroxy-2(3H)-indolone hydrobromide as a straw-brown solid. This material began to decompose with darkening at 250°.

Workup

  1. temperatureat reflux under argon for 3 hours
  2. filtrationthe reaction mixture was filtered
  3. washThe solid was washed with cold methanol

Sources & evidence

ORD record
ord-7806937cd5204b619a759f815f352094
Source dataset
uspto-grants-1982_02
Patent number
US04314944

Reaction notes

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