Hydrochloric Acid → {2-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol hydrochloride

HRID 606015Notes

Reaction equation

HRID 606015 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[CH2:22][OH:23])=[CH:12][N:11]3[CH:24]=2)=[CH:4][CH:3]=1.Cl>C(O)C.CC(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[CH2:22][OH:23])=[CH:12][N:11]3[CH:24]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67046191{2-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol

Product 1

HCID 67047014{2-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol hydrochlorideYield 76.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

40 mg of {2-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol are suspended in 1.5 ml of ethanol; 1.79 ml of a 0.1N solution of hydrochloric acid in 2-propanol are added thereto, dropwise and with stirring, and the mixture is stirred at ambient temperature for 30 minutes. The reaction mixture is then concentrated under reduced pressure. The residue solid is taken up with ethanol and the precipitate is recovered by filtration, washed with ethanol and then with diethyl ether and filter-dried. The product is dried in an oven under reduced pressure at 60° C. 17 mg of white solid are obtained. Mp=238-239° C. 1H NMR (DMSO-d6, δ in ppm): 4.50 (s, 2H); from 7.36 to 7.54 (m, 3H); from 7.60 to 7.70 (m, 3H); 7.77 (m, 1H); 7.86 (d, J=7.7 Hz, 1H); 8.14 (d, J=9.2 Hz, 2H); 8.73 (s, 1H); 8.86 (s, 1H). M+H=335.

Workup

  1. stirringthe mixture is stirred at ambient temperature for 30 minutes
  2. concentrationThe reaction mixture is then concentrated under reduced pressure
  3. filtrationthe precipitate is recovered by filtration
  4. washwashed with ethanol
  5. dry with materialwith diethyl ether and filter-dried
  6. customThe product is dried in an oven under reduced pressure at 60° C

Sources & evidence

ORD record
ord-40a23aede9bd4a9386b6712e04e271ad
Source dataset
uspto-grants-2011_03
Patent number
US07915284B2

Reaction notes

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