HCID 54195305, compound → HCID 21354733, compound

HRID 396359Notes

Reaction equation

HRID 396359 reaction equation
[N+:1]([C:4]([CH:7]([C:9]1[C:18]2[C:13](=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([C:23]([F:26])([F:25])[F:24])[CH:10]=1)[OH:8])([CH3:6])[CH3:5])([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]([CH:7]([C:9]1[C:18]2[C:13](=[C:14]([C:19]([F:20])([F:21])[F:22])[CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([C:23]([F:26])([F:24])[F:25])[CH:10]=1)[OH:8])([CH3:6])[CH3:5]

Participants

4

Reactant 1

HCID 54195305HCID 54195305, compound

Product 1

HCID 21354733HCID 21354733, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of α-(2-nitro-2-propyl)-2,8-bis(trifluoromethyl)-4-quinolinemethanol (200 mg, 0.52 mmol) in acetic acid (2 mL) was treated slowly with zinc dust, stirred at room temperature for 30 min, filtered through Celite, concentrated in vacuo and the resulting viscous oil purified by chromatography [SiO2, EtOAc] to give the title compound (63 mg, 31%) as a white solid: mp 175-176° C.; IR νmax (Nujol)/cm−1 3372, 2925, 1741, 1310,1145, 1111,756 and 684; NMR δH (400 MHz, CDC3) 0.84 (3H, s), 0.99 (3H, s), 3.37 (1H, br s), 5.69 (1H, d, J 3.9 Hz), 6.01 (1H, d, J 4.0 Hz), 7.92 (1H, t, J 8.7 Hz), 8.35 (1H, d, J 7.5 Hz) and 8.75 (1H, d, J 8.6 Hz); Anal. Calcd for C14H11ClF6N2O: C, 45.12; H, 2.97; N, 7.51. Found: C, 45.21: H, 3.29; N, 7.08.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo
  3. customthe resulting viscous oil purified by chromatography [SiO2, EtOAc]

Sources & evidence

ORD record
ord-669d18cc6d634595a7d9ea4d55a2178b
Source dataset
uspto-grants-2003_08
Patent number
US06608085B1

Reaction notes

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