Ammonium Chloride → HCID 58015562, compound

HRID 422086Notes

Reaction equation

HRID 422086 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][N:12]([C:17]4[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]([CH3:26])[CH:18]=4)[C:11](=[O:27])[C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([N:12]2[CH:13]=[CH:14][C:15]3[O:16][C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)=[CH:9][C:10]=3[C:11]2=[O:27])=[CH:18][C:19]=1[CH3:26]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58015560HCID 58015560, compound

Product 1

HCID 58015562HCID 58015562, compoundYield 92.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-(3-chlorophenyl)-5-(3-methyl-4-nitrophenyl)furo[3,2-c]pyridin-4(5H)-one (1.20 g, 3.15 mmol) in EtOH (21.2 mL) and H2O (5.16 mL) was treated with iron powder (152 g, 28.3 mmol) and NH4Cl (72.2 mg, 1.35 mmol). After stirring at reflux for 18 h, the reaction mixture was filtered through Celite® and the filtrate was concentrated to yield the title compound (1.02 g, 92%) as a light orange solid: 1H NMR (300 MHz, DMSO-d6) δ 7.95 (s, 1H), 7.84 (d, J=7.5 Hz, 1H), 7.67 (s, 1H), 7.55-7.42 (m, 3H), 6.94-6.78 (m, 3H), 6.67 (d, J=8.4 Hz, 1H), 5.11 (s, 2H), 2.09 (s, 3H).

Workup

  1. temperatureat reflux for 18 h
  2. filtrationthe reaction mixture was filtered through Celite®
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-66606f6f8fbd4b4cb196ca2baad4beb7
Source dataset
uspto-grants-2012_01
Patent number
US08101632B2

Reaction notes

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