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

HRID 586838Notes

Reaction equation

HRID 586838 reaction equation
[C:1](O)(=[O:3])C.C(O)=O.[O:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][C:23]4[NH:29][CH2:28][CH2:27][C:26]([C:30]([O:32][CH3:33])=[O:31])=[CH:25][C:24]=4[CH:34]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1>C1COCC1>[CH:1]([N:29]1[C:23]2[CH:22]=[CH:21][C:20]([C:17]3[CH:18]=[CH:19][C:14]([N:11]4[CH2:10][CH2:9][O:8][CH2:13][CH2:12]4)=[CH:15][CH:16]=3)=[CH:34][C:24]=2[CH:25]=[C:26]([C:30]([O:32][CH3:33])=[O:31])[CH2:27][CH2:28]1)=[O:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 284Formic AcidHCID 22329018methyl 7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 22328968methyl 1-formyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To anhydrous acetic acid (0.2 ml) was added dropwise formic acid (0.1 ml), under ice-cooling, and the mixture was heated to stir under nitrogen atmosphere at 50° C. for 2 hours. To the mixture was added THF (5 ml), and then to the mixture was added dropwise, under ice-cooling, a solution of methyl 7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.3 g) in THF (15 ml). The mixture was stirred at room temperature for 1.5 hours. The solvent was evaporated, and to the residue was added water. The mixture was extracted with ethyl acetate. The organic layer was washed with sodium hydrogen carbonate solution, water and saturated brine, and dried with anhydrous magnesium sulfate, and the solvent was evaporated to give methyl 1-formyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.3 g) as pale yellow crystals.

Workup

  1. temperatureunder ice-cooling
  2. temperaturethe mixture was heated
  3. additionto the mixture was added dropwise, under ice-
  4. temperaturecooling
  5. stirringThe mixture was stirred at room temperature for 1.5 hours
  6. customThe solvent was evaporated
  7. additionto the residue was added water
  8. extractionThe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with sodium hydrogen carbonate solution, water and saturated brine
  10. dry with materialdried with anhydrous magnesium sulfate
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e435e20c3f2341939b9a56b8f879ee2a
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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