Hydrochloric Acid → {3-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol hydrochloride

HRID 606011Notes

Reaction equation

HRID 606011 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:17]=[C:18]([CH2:22][OH:23])[CH:19]=[CH:20][CH:21]=4)=[CH:12][N:11]3[CH:24]=2)=[CH:4][CH:3]=1.Cl>ClCCl.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:17]=[C:18]([CH2:22][OH:23])[CH:19]=[CH:20][CH:21]=4)=[CH:12][N:11]3[CH:24]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 24856034HCID 24856034, compound

Product 1

HCID 24856062{3-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol hydrochlorideYield 169.7%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

2.37 g of {3-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol are suspended in 80 ml of dichloromethane; 4.26 ml of a 5N solution of hydrochloric acid in 2-propanol are added thereto, dropwise and with stirring, and the mixture is stirred at ambient temperature for 2 hours. The reaction mixture is then concentrated under reduced pressure. The residue solid is taken up with diisopropyl ether and the precipitate is recovered by filtration, washed with dichloromethane and then ethyl acetate and filter-dried. The solid is dissolved at ambient temperature with the minimum amount of methanol and then reprecipitated using diisopropyl ether. The precipitate is recovered by filtration and dried in an oven under reduced pressure at 60° C. 2.23 g of pale yellow solid are obtained. Mp=244-246° C. 1H NMR (DMSO-d6, δ in ppm): 4.59 (s, 2H); from 7.36 to 7.55 (m, 2H); from 7.58 to 7.74 (m, 4H); 7.96 (d, J=9.4 Hz, 1H); 8.05 (m, J=8.7 Hz, 2H); 8.14 (dd, J=9.3 Hz and 1.7 Hz, 1H); 8.70 (s, 1H); 9.15 (m, 1H). M+H=335.

Workup

  1. stirringthe mixture is stirred at ambient temperature for 2 hours
  2. concentrationThe reaction mixture is then concentrated under reduced pressure
  3. filtrationthe precipitate is recovered by filtration
  4. washwashed with dichloromethane
  5. dry with materialethyl acetate and filter-dried
  6. dissolutionThe solid is dissolved at ambient temperature with the minimum amount of methanol
  7. customreprecipitated
  8. filtrationThe precipitate is recovered by filtration
  9. customdried in an oven under reduced pressure at 60° C

Sources & evidence

ORD record
ord-02bbb390294c42d3ad13b4d0ccd73e77
Source dataset
uspto-grants-2011_03
Patent number
US07915284B2

Reaction notes

Loading…