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Sodium Carbonate → 2-Chloro-6-methoxyquinoline

HRID 456992
Notes
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Reaction equation

HRID 456992 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N+:9]([O-])=[CH:8][CH:7]=[CH:6]2.O=P(Cl)(Cl)[Cl:16].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:16][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 2538216-Methoxyquinoline N-oxide

Product 1

HCID 836472-Chloro-6-methoxyquinolineYield 46%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 6-methoxyquinoline N-oxide (5.0 g, 29 mmol) in CHCl3 (30 mL) was treated by slow addition of POCl3 (5.3 mL, 57 mmol) at 0° C. The mixture was heated at 80° C. for 14 hours. The mixture was cooled and poured onto ice. After stirring for 30 min., the aqueous layer was adjusted to pH 9 by Na2CO3 addition. The mixture was extracted with CH2Cl2. The organic layer was worked-up. HPLC (1:10 EtOAc/hexane) gave 2.5g (46%) of 2-chloro-6-methoxyquinoline as a white solid, (M+) 193(100).

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured onto ice
  3. extractionThe mixture was extracted with CH2Cl2

Sources & evidence

ORD record
ord-6766bc3f6da04c51b3c5c007744f35a5
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07186840B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes