Ammonium Chloride → HCID 28904854, compound

HRID 882057Notes

Reaction equation

HRID 882057 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][OH:11])=[C:4]([N+:12]([O-])=O)[CH:3]=1.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:12][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[NH:8][CH2:9][CH2:10][OH:11]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 14666850HCID 14666850, compound

Product 1

HCID 28904854HCID 28904854, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

2-(4-Bromo-2-nitrophenylamino)ethanol (3.20 g, 12.3 mmol) was stirred in EtOH (100 mL) and water (50 mL), and iron powder (3.45 g, 61.6 mmol) and ammonium chloride (731 mg, 13.5 mmol) were added. The mixture was heated at 85° C. for 2 h, then filtered through a pad of celite and rinsed with EtOH (500 mL). The filtrate was concentrated and purified by column chromatography eluting with methylene chloride and a 9:1 methanol/ammonium hydroxide mixture; gradient 100% methylene chloride to 85% methylene chloride, to provide the title compound (2.58 g, 91%) as a yellow oil: ESI MS m/z 231 [M+H]+.

Workup

  1. filtrationfiltered through a pad of celite
  2. washrinsed with EtOH (500 mL)
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography
  5. washeluting with methylene chloride

Sources & evidence

ORD record
ord-b7d733c171fb4dadbe75adb5bb8f854c
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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