Ammonium Chloride → HCID 58474588, compound

HRID 1400868Notes

Reaction equation

HRID 1400868 reaction equation
[F:1][C:2]1[CH:34]=[C:33]([N+:35]([O-])=O)[CH:32]=[CH:31][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]([CH3:30])[C:16]([C:19]([NH:21][CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[O:20])=[CH:17][N:18]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:35][C:33]1[CH:32]=[CH:31][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[N:15]([CH3:30])[C:16]([C:19]([NH:21][CH2:22][CH2:23][N:24]5[CH2:29][CH2:28][O:27][CH2:26][CH2:25]5)=[O:20])=[CH:17][N:18]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:34]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58474867HCID 58474867, compound

Product 1

HCID 58474588HCID 58474588, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

The reaction mixture of the nitro compound 215 (180 mg, 0.342 mmol), iron powder (162 mmol), and ammonium chloride (15.7 mg, 0.294 mmol) in EtOH/water mixture (10 mL/5 mL) was heated to reflux for 1 hr. The reaction mixture was filtered while hot. The filtrate was concentrated to give title compound 216 (130 mg, 0.262 mmol, 77% yield) as a white solid. MS: 497.5 (MH)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hr
  3. filtrationThe reaction mixture was filtered while hot
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-24304d7cdca746bf9fe6444c986025a6
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

Loading…