Ethanol → HCID 58474478, compound

HRID 1400910Notes

Reaction equation

HRID 1400910 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][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]([CH3:26])[C:16]([CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:17][N:18]=3)[S:13][C:6]=12.[Cl-].[NH4+].C(O)C>[Fe].O>[F:1][C:2]1[CH:30]=[C:29]([CH:28]=[CH:27][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]([CH3:26])[C:16]([CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:17][N:18]=3)[S:13][C:6]=12)[NH2:31]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 58474320HCID 58474320, compound

Product 1

HCID 58474478HCID 58474478, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of nitro compound 296 (907 mg, 1.932 mmol), iron powder (917 mg, 16.42 mmol) and ammonium chloride (89 mg, 1.661 mmol) in a solvent system ethanol (24.0 mL) and water (12.0 mL) was heated to 90° C. for 1 hr. The reaction mixture was filtered while hot and concentrated. The residue was purified by Biotage (MeOH.DCM, 0-20%, SNAP 25 g cartridge) to give title compound 297 (700 mg, 1.593 mmol, 82% yield) as a white solid. MS: 440 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered while hot and
  2. concentrationconcentrated
  3. customThe residue was purified by Biotage (MeOH.DCM, 0-20%, SNAP 25 g cartridge)

Sources & evidence

ORD record
ord-412806cdf64944348af60814da1c64a2
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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