Ammonium Chloride → HCID 58790403, compound

HRID 418657Notes

Reaction equation

HRID 418657 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([N+:30]([O-])=O)[CH:27]=[CH:26][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]=[CH:16][N:17]([CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[CH:18]=3)[S:13][C:6]=12.[NH4+].[Cl-]>CCO.O.[Fe]>[F:1][C:2]1[CH:29]=[C:28]([CH:27]=[CH:26][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]=[CH:16][N:17]([CH2:19][CH2:20][N:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)[CH:18]=3)[S:13][C:6]=12)[NH2:30]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58790038HCID 58790038, compound

Product 1

HCID 58790403HCID 58790403, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of nitro compound 169 (400 mg, 0.88 mmol) in EtOH/H2O (8 mL/4 mL) at 100° C. (bath) was added iron powder (420 mg, 7.48 mmol) and NH4Cl (41 mg, 0.76 mmol) and the reaction mixture was stirred vigorously at reflux temperature for an hour. The mixture was cooled to room temperature and filtered through a Celite pad. The filtrate was collected and concentrated to give the title compound 170 (4.20 mg, 88% purity) as a yellow solid. MS (m/z): 424.0 (M+H).

Workup

  1. temperatureat reflux temperature for an hour
  2. filtrationfiltered through a Celite pad
  3. customThe filtrate was collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-492345c3c9c94fa2bb43daaba205fe59
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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