Ammonium Chloride → HCID 66672833, compound

HRID 422080Notes

Reaction equation

HRID 422080 reaction equation
[NH4+].[Cl-].[Br:3][C:4]1[O:12][C:11]2[CH:10]=[CH:9][N:8]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([CH3:22])[CH:14]=3)[C:7](=[O:23])[C:6]=2[CH:5]=1>[Fe].CCO.O>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([N:8]2[CH:9]=[CH:10][C:11]3[O:12][C:4]([Br:3])=[CH:5][C:6]=3[C:7]2=[O:23])=[CH:14][C:15]=1[CH3:22]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58015543HCID 58015543, compound

Product 1

HCID 66672833HCID 66672833, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Fe powder (1.30 g, 23.2 mmol) and NH4Cl (69 mg, 1.3 mmol) were added to a suspension of 2-bromo-5-(3-methyl-4-nitrophenyl)furo[3,2-c]pyridin-4(5H)-one (896 mg, 2.58 mmol) in 4:1 EtOH/H2O (60 mL) and the resulting suspension was heated at reflux for 14 h. The suspension was filtered through Celite, while warm, and the filtrate was concentrated to afford 800 mg of crude 5-(4-amino-3-methylphenyl)-2-bromofuro[3,2-c]pyridin-4(5H)-one as a yellow solid.

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux for 14 h
  3. filtrationThe suspension was filtered through Celite
  4. temperaturewhile warm
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-77452c61d1aa4286b6aad05e6bae7a59
Source dataset
uspto-grants-2012_01
Patent number
US08101632B2

Reaction notes

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