Calcium Chloride → HCID 18428678, compound

HRID 1279632Notes

Reaction equation

HRID 1279632 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1.[Cl-].[Ca+2].[Cl-]>C(O)C.[Fe]>[NH2:10][C:8]1[CH:7]=[CH:6][C:5]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][CH:15]=2)=[C:4]([CH:9]=1)[CH2:3][N:2]([CH3:24])[CH3:1]

Participants

5

Reactant 2

HCID 5284359Calcium ChlorideHCID 18428685HCID 18428685, compound

Product 1

HCID 18428678HCID 18428678, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of the nitro compound of Example 21 (400 mg, 1.18 mmol), iron powder (591 mg, 10.6 mmol) and calcium chloride (65 mg, 0.59 mmol) in 85% aqueous ethanol (15 mL) was heated at reflux for 18 h. The reaction mixture was cooled to room temperature and filtered through Celite®, washing thoroughly with ethanol and then ethyl acetate. The solvent was removed in vacuo and the residue was purified by flash chromatography [SiO2; DCM/ MeOH/ 880 NH3 (95:5:0.5)] to give the desired aniline compound (299 mg, 82%) as a beige solid; δH(CDCI3, 300 MHz) 2.20 (6 H, s), 3.27 (2 H, s), 3.63 (2 H, brs), 6.60 (1 H, dd), 6.80 (1 H, d), 6.87 (1 H, d), 6.90 (2 H, d), 7.50 (2 H, d); MS m/z (TS+) 310 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. filtrationfiltered through Celite®
  4. washwashing thoroughly with ethanol
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatography [SiO2; DCM/ MeOH/ 880 NH3 (95:5:0.5)]

Sources & evidence

ORD record
ord-29bfc932a10d4b6eadd281471b679060
Source dataset
uspto-grants-2002_09
Patent number
US06448293B1

Reaction notes

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