Hydrochloric Acid → HCID 21034936, compound

HRID 1833134Notes

Reaction equation

HRID 1833134 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[N:5]([CH:12]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:23]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)[CH2:6][CH:7](OC)OC)[CH3:2].Cl>CC(C)=O.O>[CH2:1]([O:3][C:4]([N:5]1[CH:6]=[CH:7][C:27]2[C:22](=[CH:23][C:24]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[C:25]([O:28][CH3:29])[CH:26]=2)[CH:12]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)=[O:38])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21034940HCID 21034940, compound

Product 1

HCID 21034936HCID 21034936, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

[1-(3-Benzyloxy-4-methoxy-phenyl)-2-(3-methoxy-phenyl)-ethyl]-(2,2-dimethoxy-ethyl)-carbamic acid ethyl ester (3.15 g, 6.01 mmol) was dissolved in acetone (125 mL) at 0° C., and 6M aqueous hydrochloric acid (25 mL) was added dropwise. After the addition was complete, the mixture was stored at 0° C. overnight (14 hours). The mixture was warmed to room temperature and stirred×4 hours. The mixture was cooled in an ice bath and diluted with water (150 mL). The mixture was extracted with ethyl acetate (3×60 mL). The combined organic extracts were washed with water (60 mL), saturated aqueous sodium chloride solution (60 mL) and dried over anhydrous magnesium sulfate. Concentration of the solvent gave an oily solid that was crystallized from ethyl acetate/hexanes to give 7-benzyloxy-6-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester (1.32 g, 2.87 mmol, 48%) as a white solid.

Workup

  1. additionAfter the addition
  2. custom(14 hours)
  3. temperatureThe mixture was cooled in an ice bath
  4. extractionThe mixture was extracted with ethyl acetate (3×60 mL)
  5. washThe combined organic extracts were washed with water (60 mL), saturated aqueous sodium chloride solution (60 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customConcentration of the solvent gave an oily solid
  8. customthat was crystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-855bef07717d48d892b03ff6cb42ccfd
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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