Sodium Hydroxide → HCID 23042865, compound

HRID 2165533Notes

Reaction equation

HRID 2165533 reaction equation
[OH-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4]1.Br[CH2:16][CH:17]1[CH2:19][CH2:18]1>CC(C)=O.O>[CH:17]1([CH2:16][N:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:12]([OH:14])=[O:13])=[CH:4]2)[CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 69867Indole-3-Carboxylic AcidHCID 81503Bromomethylcyclopropane

Product 1

HCID 23042865HCID 23042865, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Powdered sodium hydroxide (10 g) was added cautiously to a stirred solution of indole-3-carboxylic acid (5 g) and (bromomethyl)cyclopropane (10 g) in dry acetone (50 ml). The mixture was stirred for 24 hours at room temperature then diluted with water (250 ml) and washed with dichloromethane (2×100 ml). The aqueous phase acidified to pH 2 and the precipitate isolated and dried (6.3 g), m.p. 157° C.; δH (360 MHz, CDCl3) 0.02-0.04 (2H, m, CH2), 0.18-0.28 (2H, m, CH2), 0.83-0.89 (1H, m, CH), 3.57 (2H, d, J=7 Hz, NCH2), 6.7-6.8 (2H, m, H-5, H-6), 6.9 (1H, d, J=7 Hz, H-7), 7.55 (1H, s, H-2), 7.72 (1H, d, J=7 Hz, H- 4); m/z 215 (M+, 100%), 174 (60), 144 (40).

Workup

  1. washwashed with dichloromethane (2×100 ml)
  2. customthe precipitate isolated
  3. customdried (6.3 g), m.p. 157° C.

Sources & evidence

ORD record
ord-a2d7e8028065489c93fa64ce0cf6486d
Source dataset
uspto-grants-1990_07
Patent number
US04940703

Reaction notes

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