Ammonium Chloride → HCID 43115327, compound

HRID 386868Notes

Reaction equation

HRID 386868 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([NH:6][CH2:7][CH:8]2[CH2:10][CH2:9]2)=[C:4]([N+:13]([O-])=O)[CH:3]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[C:5]([NH:6][CH2:7][CH:8]2[CH2:10][CH2:9]2)=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 29274404HCID 29274404, compound

Product 1

HCID 43115327HCID 43115327, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-N-(cyclopropylmethyl)-2-nitroaniline (11.96, 44 mol), iron (12.3 g, 220 mmol) and ammonium chloride (236 mg, 4.4 mmol) in ethanol (120 mL) and water (40 mL) is stirred at 100° C. for 3 h. After cooling to room temperature, the mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is dissolved in ethyl acetate (100 mL) and water (50 mL). The organic layer is separated, washed with brine (20 mL), dried over MgSO4, filtered and the filtrate is concentrated under reduced pressure to afford 9.6 g of 4-bromo-N1-(cyclopropylmethyl)benzene-1,2-diamine as an oil. Yield: 90%, ES-MS: 241/243 [M+H].

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in ethyl acetate (100 mL)
  5. customThe organic layer is separated
  6. washwashed with brine (20 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7ed91c762524d28863a43902a7e4ebc
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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