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Dichloromethane → 2-cyclopropanecarboxamido-5-Bromo-4-Methyl-3-nitropyridine

HRID 744974
Notes
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Reaction equation

HRID 744974 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[C:5]([Br:12])=[CH:4][N:3]=1.C1(C)C(C)=CC=CC=1.[CH:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1.ClCCl>CN(C)C1C=CN=CC=1.O>[CH:21]1([C:24]([NH:1][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[C:5]([Br:12])=[CH:4][N:3]=2)=[O:25])[CH2:23][CH2:22]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7237O-XyleneHCID 77637Cyclopropanecarbonyl chlorideHCID 72132072-Amino-5-bromo-4-methyl-3-nitropyridine

Product 1

HCID 109794822-cyclopropanecarboxamido-5-Bromo-4-Methyl-3-nitropyridineYield 88.1%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture comprising 10 g (43.1 mmol) of 2-amino-5-bromo-4-methyl-3-nitropyridine, 6.3 g of 4-dimethylaminopyridine and xylene (50 ml) was heated at 110° C. in a nitrogen atmosphere. 5 g (47.4 mmol) of cyclopropanecarbonyl chloride was dropwise added thereto, followed by further stirring at 110° C. for 2 hours. The reaction mixture was brought to room temperature, followed by the addition of dichloromethane (200 ml) and water (50 ml). The organic phase was separated and the aqueous phase was further extracted with dichloromethane (50 ml). The organic phases were combined and washed with water (50 ml). The resulting organic phase was dried over anhydrous magnesium sulfate and concentrated to give a crude crystal. It was recrystallized from chloroform/ethyl acetate to give 11.4 g of the title compound (yield 88%).

Workup

  1. customwas brought to room temperature
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was further extracted with dichloromethane (50 ml)
  4. washwashed with water (50 ml)
  5. dry with materialThe resulting organic phase was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give a crude crystal
  8. customIt was recrystallized from chloroform/ethyl acetate

Sources & evidence

ORD record
ord-77f3a031c1214ac984c3a0d640fdef40
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05559236

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes