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Acetic Acid → methyl 1-formyl-7-[4-(2-propoxy)ethoxyphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 586876
Notes
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Reaction equation

HRID 586876 reaction equation
[C:1](O)(=[O:3])C.C(O)=O.[CH3:8][CH:9]([O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][C:24]3[NH:30][CH2:29][CH2:28][C:27]([C:31]([O:33][CH3:34])=[O:32])=[CH:26][C:25]=3[CH:35]=2)=[CH:17][CH:16]=1)[CH3:10].C(OC=O)=O>C1COCC1>[CH:1]([N:30]1[C:24]2[CH:23]=[CH:22][C:21]([C:18]3[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][O:11][CH:9]([CH3:8])[CH3:10])=[CH:16][CH:17]=3)=[CH:35][C:25]=2[CH:26]=[C:27]([C:31]([O:33][CH3:34])=[O:32])[CH2:28][CH2:29]1)=[O:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 284Formic AcidHCID 9548680Formic anhydrideHCID 22329022HCID 22329022, compound

Product 1

HCID 22329024methyl 1-formyl-7-[4-(2-propoxy)ethoxyphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
3×

Conditions

Temperature
55 °C

Procedure

To anhydrous acetic acid (0.51 ml) was added formic acid, (0.25 ml) at 0° C., and the mixture was stirred at 55° C. for 2 hours, air-cooled and diluted with THF (10 ml). In THF (15 ml) was dissolved methyl 7-[4-(2-propoxy)ethoxyphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate (462 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 2 hours, and the solvent was evaporated under reduced pressure. 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-(2-propoxy)ethoxyphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate (496 mg) as white crystals.

Workup

  1. temperatureair-cooled
  2. stirringThe mixture was stirred at room temperature for 2 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-875aba5f0f4d484a881b5198b746e910
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06936602B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes