Hydrochloric Acid → HCID 71255069, compound

HRID 540323Notes

Reaction equation

HRID 540323 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4]([N:13]2[CH2:19][CH2:18][CH2:17][C:16]3[CH:20]=[C:21]([C:24]([O:26]C)=[O:25])[CH:22]=[CH:23][C:15]=3[CH2:14]2)[CH:3]=1.CO.[OH-].[Na+].Cl>O.C(OCC)(=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4]([N:13]2[CH2:19][CH2:18][CH2:17][C:16]3[CH:20]=[C:21]([C:24]([OH:26])=[O:25])[CH:22]=[CH:23][C:15]=3[CH2:14]2)[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 71255477HCID 71255477, compound

Product 1

HCID 71255069HCID 71255069, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-(4,6-dichloroquinolin-2-yl)-2,3,4,5-tetrahydro-1H-2-benzazepine-7-carboxylate (156 mg, 0.39 mmol) was added into the mixture of methanol (5 mL) and sodium hydroxide (5 M, 2 mL). The reaction mixture was stirred at room temperature overnight. After that, the reaction was diluted with 20 mL of water, acidified with 2 M of hydrochloric acid to pH 6 and diluted with ethyl acetate (30 mL). The organic layer was separated and washed with water. The solvent was dried over sodium sulfate and concentrated in vacuo to give a residue which was purified by column chromatography on silica gel to give 135 mg of product. MS obsd. (ESI+) [(M+H)+] 387.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialThe solvent was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue which
  6. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0b2671ef6ab44ee1abdea131ae611b0e
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

Loading…