Water → HCID 22148907, compound

HRID 1819764Notes

Reaction equation

HRID 1819764 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:19]([O-])=O)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.[NH4+].[Cl-].O>CCO.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:19])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 23503311HCID 23503311, compound

Product 1

HCID 22148907HCID 22148907, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of nitrobenzene 51 (2.07 g) and NH4Cl (1.84 g) in EtOH (40 mL)-H2O (10 mL), was added iron powder (1.92 g). The mixture was heated to reflux for 1 h. After cooling the reaction mixture was filtered through short celite pad. The filtrate was concentrated, diluted with sat.NaHCO3 (30 mL) and extracted with AcOEt (30 mL). The combined organic layers were washed with brine (30 mL) and dried over Na2SO4. Concentration of the solvent afforded the aniline 52 (1.77 g, 95%) as a yellow solid. 1H NMR (300 MHz/CDCl3) δ 3.77 (2H, brs), 6.63 (1H, dd, J=2.7 Hz, J=8.6 Hz), 6.83 (1H, d, J=2.7 Hz), 6.99 (1H, d, J=8.6 Hz), 7.24 (1H, d, J=2.8 Hz), 7.49 (1H, m), 7.56-7.64 (2H, m), 8.08 (1H, m), 8.86 (1H, J=2.8 Hz)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. temperatureAfter cooling the reaction mixture
  4. filtrationwas filtered through short celite pad
  5. concentrationThe filtrate was concentrated
  6. additiondiluted
  7. extractionNaHCO3 (30 mL) and extracted with AcOEt (30 mL)
  8. washThe combined organic layers were washed with brine (30 mL)
  9. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-ab692efbad054b22936968e9b294240d
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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