Acetic Acid → methyl 1-formyl-7-(4-propoxyphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 586869Notes

Reaction equation

HRID 586869 reaction equation
[C:1](O)(=[O:3])C.C(O)=O.[CH2:8]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]3[NH:27][CH2:26][CH2:25][C:24]([C:28]([O:30][CH3:31])=[O:29])=[CH:23][C:22]=3[CH:32]=2)=[CH:14][CH:13]=1)[CH2:9][CH3:10].C(OC=O)=O>C1COCC1>[CH:1]([N:27]1[C:21]2[CH:20]=[CH:19][C:18]([C:15]3[CH:14]=[CH:13][C:12]([O:11][CH2:8][CH2:9][CH3:10])=[CH:17][CH:16]=3)=[CH:32][C:22]=2[CH:23]=[C:24]([C:28]([O:30][CH3:31])=[O:29])[CH2:25][CH2:26]1)=[O:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 284Formic AcidHCID 9548680Formic anhydrideHCID 22328960methyl 7-(4-propoxyphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 22328923methyl 1-formyl-7-(4-propoxyphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

To anhydrous acetic acid (0.65 ml) was added formic acid (0.32 ml) at 0° C., and the mixture was stirred at 60° C. for 2 hours, air-cooled and diluted with THF (10 ml). In THF (10 ml) was dissolved methyl 7-(4 propoxyphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (520 mg), and the solution was added dropwise to the previously prepared solution of formic anhydride in THF, at 0° C. The mixture was stirred at room temperature for 1.5 hours. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate, washed with saturated sodium hydrogen carbonate solution, water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give crystals, which were washed with ethyl acetate/hexane to give methyl 1-formyl-7-(4-propoxyphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (563 mg) as white crystals.

Workup

  1. temperatureair-cooled
  2. stirringThe mixture was stirred at room temperature for 1.5 hours
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with saturated sodium hydrogen carbonate solution, water and saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customto give crystals, which
  9. washwere washed with ethyl acetate/hexane

Sources & evidence

ORD record
ord-e324cb41e2f14621bb6eb031d6442913
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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