1-Chloro-2-iodobenzene → 1-(2-Chlorophenyl)-3-(2-hydroxyiminopropyl)indole

HRID 1580717Notes

Reaction equation

HRID 1580717 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH2:25][C:26](=O)[CH3:27])=[CH:17]1.ClC1C=CC=CC=1I>C(O)C>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH2:25][C:26](=[N:2][OH:3])[CH3:27])=[CH:17]1

Participants

6

Reactant 4

HCID 119931-Chloro-2-iodobenzeneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 215435021-(2-Chlorophenyl)-3-(2-oxopropyl)indole

Product 1

HCID 539360231-(2-Chlorophenyl)-3-(2-hydroxyiminopropyl)indoleYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.1 G (0.03 mole) of hydroxylamine hydrochloride and 2.1 g of sodium acetate are added, all at once, to 5.8 g (0.02 mole) of 1-(2-chlorophenyl)-3-(2-oxopropyl)indole prepared as described in example 1 but using 2-chloroiodobenzene instead of iodobenzene are dissolved in 50 ml of ethanol. The mixture is stirred overnight. The oxime formed is then filtered, washed in water and recrystallised, after drying, from 30 ml of di-isopropyl ether. Product = 4.3 g: Melting point (k) = 127°. Yield = 71%.

Sources & evidence

ORD record
ord-29a0b1b2d1cf4bf7ad950c7ba4e78e3c
Source dataset
uspto-grants-1976_01
Patent number
US03933853

Reaction notes

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