Hydrochloric Acid → 5-Iodo-8-quinolinol

HRID 1479929Notes

Reaction equation

HRID 1479929 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Na+].[I-:13].[OH-].[Na+].N#N.[O-]Cl.[Na+].Cl>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([I:13])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 19238-HydroxyquinolineHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 23665760Sodium Hypochlorite

Product 1

HCID 961115-Iodo-8-quinolinol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of 8-hydroxyquinoline (25.0 g, 172.3 mmol), NaI (26.0 g, 172.5 mmol) and NaOH (6.9 g, 172.5 mmol) in MeOH (750 ml) is degassed by passing-through of N2 for 60 min. at room temperature. After cooling to −30° C., a 5% aqueous NaOCl solution (250 ml) is added dropwise. The mixture is stirred vigorously at −30° C. for 30 min. and then neutralised using a 10% aqueous HCl solution. The precipitated product is filtered off. After two recrystallisations from MeOH/heptane (1:1, v/v), a pale-yellow solid is obtained (14 g, 27%).

Workup

  1. filtrationThe precipitated product is filtered off
  2. customAfter two recrystallisations from MeOH/heptane (1:1
  3. customv/v), a pale-yellow solid is obtained (14 g, 27%)

Sources & evidence

ORD record
ord-aeb6111ae2cc4614ba2128783487c2a6
Source dataset
uspto-grants-2016_08
Patent number
US09409883B2

Reaction notes

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