Methanol → HCID 66888478, compound

HRID 1895552Notes

Reaction equation

HRID 1895552 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:20]([C:21]([OH:23])=[O:22])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:29]O>>[CH2:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:19][CH:20]([C:21]([O:23][CH3:29])=[O:22])[N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 42347112,3(1H)-Isoquinolinedicarboxylic acid, 3,4-dihydro-, 2-(phenylMethyl) ester

Product 1

HCID 66888478HCID 66888478, compound

Procedure

Step-1: A mixture of 2-((benzyloxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (2 g, 6.42 mmol) and conc. sulfuric acid (0.45 mL) in methanol was refluxed overnight. The reaction mixture was concentrated, neutralized with aq. sodium bicarbonate and extracted with DCM. The DCM layer was washed with brine, dried over anhydrous sodium sulfate and evaporated to afford 2-benzyl 3-methyl 3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate. MS (ES+): m/z 348.12 [M+Na]+

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with DCM
  4. washThe DCM layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-7482a9c1eb954eb0926a47e617478b2e
Source dataset
uspto-grants-2013_08
Patent number
US08513433B2

Reaction notes

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