Hydrochloric Acid → 2-oxo-2-(5-phenoxy-1H-indol-3-yl)acetamide

HRID 1371892Notes

Reaction equation

HRID 1371892 reaction equation
[O:1]=[C:2]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:13]=2)[NH:8][CH:7]=1)[C:3](Cl)=[O:4].[OH-].[NH4+:23].Cl>>[O:1]=[C:2]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:13]=2)[NH:8][CH:7]=1)[C:3]([NH2:23])=[O:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 210714422-Oxo-(5-phenoxy-1H-indol-3-yl)acetyl chloride

Product 1

HCID 210714372-oxo-2-(5-phenoxy-1H-indol-3-yl)acetamideYield 96.4%

Procedure

Combine 2-oxo-(5-phenoxy-1H-indol-3-yl)acetyl chloride (2.15 g, 7.18 mmol), and ammonium hydroxide (28–30%, 32 ml, 680 mmol) and stir for 2 hours. Pour the reaction mixture into 10% (aq.) HCl, extract with dichloromethane, combine the organic layers and dry over Na2SO4, evaporate solvent in vacuo to give 1.94 g (96%) of title compound: 1H NMR (300 MHz, CDCl3) 4.87 (s, 2H), 7.51–7.91 (m, 7H), 8.13–8.24 (m, 3H).

Workup

  1. extractionextract with dichloromethane
  2. dry with materialdry over Na2SO4
  3. customevaporate solvent in vacuo

Sources & evidence

ORD record
ord-4fa060e2b2934bb785e647f78f87012a
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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