Ammonium Chloride → HCID 57919557, compound

HRID 1952474Notes

Reaction equation

HRID 1952474 reaction equation
[F:1][C:2]1[CH:37]=[C:36]([N+:38]([O-])=O)[CH:35]=[CH:34][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[C:16]([CH:31]=[CH:32][CH:33]=3)[CH2:17][CH2:18][N:19]([CH2:27][CH2:28][O:29][CH3:30])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[S:13][C:6]=12.[Cl-].[NH4+]>CO.O.[Zn]>[NH2:38][C:36]1[CH:35]=[CH:34][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[CH:15]=[C:16]([CH:31]=[CH:32][CH:33]=4)[CH2:17][CH2:18][N:19]([CH2:27][CH2:28][O:29][CH3:30])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:23])[CH3:24])[S:13][C:6]=23)=[C:2]([F:1])[CH:37]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 57919635HCID 57919635, compound

Product 1

HCID 57919557HCID 57919557, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To nitro compound 155 (0.44 g, 0.78 mmol) and zinc dust (0.65 g, 10 mmol) in methanol (50 mL) was added ammonium chloride (0.075 g, 1.4 mmol) in water (6 mL). The resulting mixture was heated to reflux for 2 h, then cooled, filtered through celite and concentrated. Silica gel chromatography (70% ethyl acetate/hexanes) afforded title compound 156 (0.36 g, 88% yield). MS (m/z): 538.3 (M+H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 h
  3. temperaturecooled
  4. filtrationfiltered through celite and
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fe2de80ad4334f229d4caadeadc61d3d
Source dataset
uspto-grants-2013_03
Patent number
US08404846B2

Reaction notes

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