Hydrochloric Acid → HCID 23023856, compound

HRID 851867Notes

Reaction equation

HRID 851867 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:12]([OH:14])=O)#[N:8].[NH2:23][C:24]1[C:25]([Cl:34])=[C:26]([CH:31]=[CH:32][CH:33]=1)[C:27]([O:29][CH3:30])=[O:28].C(N(CC)CC)C.Cl>ClCCl.C1COCC1.C1(C)C=CC=CC=1.CN(C=O)C>[Cl:34][C:25]1[C:24]([NH:23][C:12](=[O:14])[C:11]2[CH:15]=[CH:16][C:17]([O:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[C:9]([C:7]#[N:8])[CH:10]=2)=[CH:33][CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15132848Methyl 3-amino-2-chlorobenzoateHCID 230238503-Cyano-4-(2-methylpropoxy)benzoic acid

Product 1

HCID 23023856HCID 23023856, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (889 mg, 7.0 mmol) was dropwise added to a solution of 3-cyano-4-isobutyloxybenzoic acid (767 mg, 3.5 mmol) in dichloromethane (10 mL) under cooling with ice. Subsequently, a catalytic amount of DMF was added. The mixture was then stirred for one hour at room temperature, heated under reflux for 3 hours, and placed under reduced pressure to distill the solvent off. Toluene was added to the residue and the solvent was distilled off under reduced pressure. THF (10 mL) was added to the residue. Further, a solution of methyl 3 amino-2-chlorobenzoate (497 mg, 2.68 mmol) and triethylamine (1.39 mL, 10 mmol) in THF (10 mL). The resulting mixture was stirred for 14 hours at room temperature, and toluene and aqueous 1M hydrochloric acid were added. The organic portion was taken out, washed with aqueous 1M hydrochloric acid and aqueous saturated sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, and placed under reduced pressure to distill the solvent off.

Workup

  1. temperatureunder cooling with ice
  2. temperatureheated
  3. temperatureunder reflux for 3 hours
  4. distillationto distill the solvent off
  5. additionToluene was added to the residue
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTHF (10 mL) was added to the residue
  8. stirringThe resulting mixture was stirred for 14 hours at room temperature
  9. washwashed with aqueous 1M hydrochloric acid and aqueous saturated sodium hydrogen carbonate
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationto distill the solvent off

Sources & evidence

ORD record
ord-0338b59f463e49dba96a30b64fdeda9e
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

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