Hydrochloric Acid → 8-Quinolinol, 5-(chloromethyl)-, hydrochloride (1:1)

HRID 574283Notes

Reaction equation

HRID 574283 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3][CH:2]=1.[ClH:12].[CH2:13]=O>O>[ClH:12].[Cl:12][CH2:13][C:6]1[CH:7]=[CH:8][C:9]([OH:11])=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 19238-Hydroxyquinoline

Product 1

HCID 122695968-Quinolinol, 5-(chloromethyl)-, hydrochloride (1:1)Yield 77.78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of commercially available compound 10, 8-quinolinol (7.3 g, 50.29 mmol), 8 mL of 32% HCl in water, and 8 mL of 37% formaldehyde in water at 0° C. was treated with hydrogen chloride gas for 6 h. The solution was allowed to stand at room temperature for 2 h without stirring. The yellow solid obtained was collected on a filter, washed with 90% alcohol, and dried under vacuum to give 5-chloromethyl-8-quinolinol hydrochloride 11 as yellow solid (9.0 g, 77.78%). 1H NMR of HCl salt (400 MHz, DMSO) δ ppm 5.30 (s, 2H), 7.49-7.51 (d, 1H, J=8 Hz), 7.83-7.85 (d, 1H, J=8 Hz), 8.08-8.12 (dd, 1H, J1=5.6 Hz, J2=8.8), 9.098-9.110 (d, 1H, J=4.8 Hz), 9.193-9.213 (d, 1H, J=8 Hz)

Workup

  1. customThe yellow solid obtained
  2. customwas collected on a filter
  3. washwashed with 90% alcohol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-166a5d9090bb43aaa67b1bb40cee6301
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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