Acetic Anhydride → HCID 178497281, compound

HRID 38488Notes

Reaction equation

HRID 38488 reaction equation
CC(OC(C)=O)=O.CC([O-])=O.[K+].[NH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[CH2:24][CH3:25])[C:17]([O:19][CH3:20])=[O:18].C1OCCOCCOCCOCCOCCOC1.C(O[N+:49]([O-])=O)C(C)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl.O.C1COCC1.CO>[CH3:25][C:24]1[C:23]2[C:14](=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=2)[NH:13][N:49]=1

Participants

11

Reactant 6

HCID 7918Acetic AnhydrideHCID 10974Isobutyl nitrateHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 517044Potassium Acetate2×HCID 13399999Methyl 3-amino-4-ethylbenzoate

Product 1

HCID 178497281HCID 178497281, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

Ac2O (0.579 ml, 6.14 mmol) was added to a stirred mixture of KOAc (361 mg, 3.68 mmol) and methyl 3-amino-4-ethylbenzoate (550mg, 3.07 mmol) in CHCl3 (5 ml) and the mixture was stirred at 90° C. for 2 h. KOAc (361 mg, 3.68 mmol), 18-crown-6 ether (81 mg, 0.307 mmol) and isobutylnitrate (719 mg, 6.14 mmol) were added thereto at room temperature and the mixture was further stirred at 90° C. for 2 h. The reaction mixtuer was diluted with chloroform and H2O, the organic layer was washed with water, brine, and dried over MgSO4. After filteration and evaporation, the residue was diluted with THF (5.00 ml) and MeOH (5.00 ml), and K2CO3 (848 mg, 6.14 mmol) was added thereto at room temperature. After the mixture was stirred for 2 h. at room temperature, CHCl3 and H2O was added thereto. The organic layer was washed with H2O, brine, and dried over MgSO4. After filteration and evaporation, the reside was puritied by silicagel column chromatography (hexane/EtOAc) to give intended compound as a pale brown solid.

Workup

  1. stirringat room temperature and the mixture was further stirred at 90° C. for 2 h
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over MgSO4
  4. customAfter filteration and evaporation
  5. additionwas added
  6. customat room temperature
  7. stirringAfter the mixture was stirred for 2 h. at room temperature
  8. washThe organic layer was washed with H2O, brine
  9. dry with materialdried over MgSO4
  10. customAfter filteration and evaporation
  11. customto give

Sources & evidence

ORD record
ord-4fec3f76bc8444e8909bfaad57ee46ee
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Reaction notes

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