Hydrochloric Acid → HCID 22328926, compound

HRID 587033Notes

Reaction equation

HRID 587033 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([CH2:8][N:9]2[C:15]3[CH:16]=[CH:17][C:18]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH3:29])=[CH:22][CH:21]=4)=[CH:19][C:14]=3[CH:13]=[C:12]([C:30]([O:32]C)=[O:31])[CH2:11][CH2:10]2)[CH:5]=[N:4]1)[CH3:2].[OH-].[Na+].O.Cl>O1CCCC1.CO>[CH2:1]([N:3]1[CH:7]=[C:6]([CH2:8][N:9]2[C:15]3[CH:16]=[CH:17][C:18]([C:20]4[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][CH3:29])=[CH:24][CH:25]=4)=[CH:19][C:14]=3[CH:13]=[C:12]([C:30]([OH:32])=[O:31])[CH2:11][CH2:10]2)[CH:5]=[N:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22329208HCID 22329208, compound

Product 1

HCID 22328926HCID 22328926, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-[(1-ethylpyrazol-4-yl)methyl]-7-(4-propoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylate (370 mg) in a mixture of tetrahydrofuran (24 ml) and methanol (24 ml) was added 1N sodium hydroxide solution (8 ml), and the mixture was stirred at room temperature for 1 day. Then, to the mixture was added water at 0° C., and 1N hydrochloric acid was further added to neutral, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure to give 1-[(1-ethylpyrazol-4-yl)methyl]-7-(4-propoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (330 mg) as yellow oil.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a9ba903148fc4837a167d46571663698
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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