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

HRID 573971

Reaction equation

HRID 573971 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)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 14.6 g (0.1 mol) of 8-quinolinol, 16 mL of 32% HCl in water, and 16 mL (0.1 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 A (19.0 g, 98%): 1H NMR (250 MHz, CDCl3, δ) 5.32 (s, 2H), 7.53 (m, 1H), 7.85 (m, 2H), 8.12 (m, 1H), 9.12 (m, 1H), 9.28 (m, 1H).

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-208cc568f2f84b298b7cfeefc9fcb376
Source dataset
uspto-grants-2015_05
Patent number
US09034303B2

Linked notes

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