Calcium Chloride → HCID 18511411, compound

HRID 1370336Notes

Reaction equation

HRID 1370336 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:12]=[C:11]([CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-])=O)[OH:14])[C:10]2[C:5](=[C:6]([C:24]([F:27])([F:26])[F:25])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.[Cl-].[Cl-].[Ca+2]>CCO.[Zn]>[NH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH:13]([C:11]1[C:10]2[C:5](=[C:6]([C:24]([F:25])([F:26])[F:27])[CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]([C:2]([F:29])([F:1])[F:28])[CH:12]=1)[OH:14]

Participants

5

Reactant 2

HCID 5284359Calcium ChlorideHCID 9888121HCID 9888121, compound

Product 1

HCID 18511411HCID 18511411, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A solution of 2,8-bis(trifluoromethyl)-α-(2-nitrophenyl)-4-quinolinemethanol (636 mg, 1.53 mmol) in EtOH (30 mL) was treated with zinc dust (994 mg, 15.3 mmol) and CaCl2 (170 mg, 1.53 mmol), refluxed for 3 h, cooled, filtered through a pad of celite, concentrated in vacuo, purified by chromatography [SiO2; CH2Cl2] and the resulting solid recrystallised from CH2Cl2/heptane to give the title compound (202 mg, 34%) as a cream solid: mp 145.9-146.2° C.; IR νmax (Nujol)/cm−1 3413, 3339, 3094, 2924, 2854, 1611, 1586, 1462, 1313, 1295, 1155, 1132, 1111 and 1073; NMR δH (400 MHz, CDCl3) 1.40-1.79 (1H, s), 2.39-3.14 (1H, s), 3.84-4.58 (2H, s), 6.48-6.50 (1H, m), 6.59-6.62 (2H, m), 6.83 (1H, d, J 6.5 Hz), 7.15-7.18 (1H, m), 7.59 (1H, t, J 8.1 Hz), 7.99 (1H, d, J 9.0 Hz), 8.12 (1H, d, J 6.9 Hz) and 8.18 (1H, s); Anal. Calcd for C18H12F6N2O.0.25 H2O: C, 55.32; H, 3.22; N, 7.17. Found: C, 55.33; H, 3.34; N, 7.03.

Workup

  1. temperaturerefluxed for 3 h
  2. temperaturecooled
  3. filtrationfiltered through a pad of celite
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography [SiO2; CH2Cl2]
  6. customthe resulting solid recrystallised from CH2Cl2/heptane

Sources & evidence

ORD record
ord-28db7cee93334cee8e7a72156bbd6553
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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