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O-Xylene → 4-Cyclopropyl-3-nitropyridine

HRID 1844033
Notes
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Reaction equation

HRID 1844033 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH:11]1(B(O)O)[CH2:13][CH2:12]1.C1(C)C(C)=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CCCCCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[CH:11]1([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:13][CH2:12]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7237O-XyleneHCID 11430Potassium CarbonateHCID 27357814-Chloro-3-nitropyridineHCID 2760897Cyclopropylboronic acid

Product 1

HCID 668018544-Cyclopropyl-3-nitropyridineYield 736.3%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 8058HexaneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

4-Chloro-3-nitropyridine (100 mg, 0.630 mmol) and cyclopropyl boronic acid (10.0 mg, 0.091 mmol) were added to a solution of xylene (3 mL) previously purged with argon (10 min). The reaction mixture was purged with argon for a further 15 mins, followed by the addition of potassium carbonate (174.35 mg, 1.26 mmol) and Pd(PPh3)4 (34.5 mg, 0.063 mmol). The resulting mixture was heated to reflux at 130° C. overnight. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mixture was cooled and concentrated to afford the crude product. Purification by column chromatography on silica gel (15% ethyl acetate in hexane) afforded 110 mg of the product (100% yield). LCMS: 99.09%, m/z=165 (M+1)

Workup

  1. custompreviously purged with argon (10 min)
  2. customThe reaction mixture was purged with argon for a further 15 mins
  3. temperatureThe resulting mixture was heated
  4. temperatureThe reaction mixture was cooled
  5. concentrationconcentrated
  6. customto afford the crude product
  7. customPurification by column chromatography on silica gel (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-30041b14b6114ed2b7384ac79b9e3e78
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946260B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes