Ammonium Hydroxide → 4-Chloro-7-iodo-6-methylquinoline

HRID 1006166Notes

Reaction equation

HRID 1006166 reaction equation
[I:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH:7]=[CH:8][NH:9]2)=[CH:4][C:3]=1[CH3:13].[Cl-:14].[P+]=O.[OH-].[NH4+]>CN(C)C=O>[Cl:14][C:6]1[C:5]2[C:10](=[CH:11][C:2]([I:1])=[C:3]([CH3:13])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 220545057-Iodo-6-methylquinolin-4(1H)-oneHCID 178527006HCID 178527006, compound

Product 1

HCID 220545044-Chloro-7-iodo-6-methylquinolineYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7-iodo-6-methyl-1H-quinolin-4-one (5.12 g, 18.0 mmol), phosphorus oxide chloride (14 mL) and N,N-dimethylformamide (1 mL) was stirred at 60° C. for 80 min, then poured onto ice and carefully neutralized with 25% aq. ammonium hydroxide solution. The suspension was extracted three times with dichloromethane, the combined organic phase was washed with brine, dried (MgSO4), and evaporated to afford the title compound (5.33 g, 98%). Light brown solid, ISP-MS: m/e=304.1 ([M+H]+).

Workup

  1. additionpoured onto ice
  2. extractionThe suspension was extracted three times with dichloromethane
  3. washthe combined organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-718ab532e9ec4affb8685fc38da72600
Source dataset
uspto-grants-2004_09
Patent number
US06787558B2

Reaction notes

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