4-Amino-2-chloro-3-methylbenzonitrile → HCID 11988441, compound

HRID 1157665Notes

Reaction equation

HRID 1157665 reaction equation
CS(O[CH:6]([CH2:21][CH3:22])[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)=O.[NH2:23][C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([Cl:32])[C:25]=1[CH3:33]>C1(C)C=CC=CC=1>[Cl:32][C:26]1[C:25]([CH3:33])=[C:24]([N:23]2[CH:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:8][CH2:7][CH:6]2[CH2:21][CH3:22])[CH:31]=[CH:30][C:27]=1[C:28]#[N:29]

Participants

4

Reactant 2

HCID 218754134-Amino-2-chloro-3-methylbenzonitrileHCID 59511924HCID 59511924, compound

Product 1

HCID 11988441HCID 11988441, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dissolve methanesulfonic acid 4-methanesulfonyloxy-1-phenyl-hexyl ester (381 mg, 1.09 mmol) in toluene (10 mL) in a reaction tube. Add 4-amino-2-chloro-3-methylbenzonitrile (363 mg, 2.18 mmol), purge with nitrogen and cap. Heat the reaction in a 120° C. oil bath for 17 h. Cool, concentrate, and purify by silica gel chromatography using 5-30% EtOAc/hexanes to obtain 7 mg (1%) of the title compound (a mixture of 4 isomers) as a clear oil. MS (ESI+): 325 (M+1)+.

Workup

  1. customcap
  2. temperatureHeat
  3. customthe reaction in a 120° C. oil bath for 17 h
  4. temperatureCool
  5. concentrationconcentrate
  6. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-3eed3b894358456182fb1169d085a208
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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