Benzyl chloroformate → 2,3(1H)-Isoquinolinedicarboxylic acid, 3,4-dihydro-, 2-(phenylMethyl) ester

HRID 1732023Notes

Reaction equation

HRID 1732023 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([C:11]([OH:13])=[O:12])[NH:2]1.[C:14](Cl)(=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[OH-].[Na+]>[C:14]([N:2]1[CH:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:23]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 954891,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 42347112,3(1H)-Isoquinolinedicarboxylic acid, 3,4-dihydro-, 2-(phenylMethyl) ester

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

188 g (1.05 moles) of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid were added to 1,050 ml of 1N NaOH at 0° and then at this temperature, 100 ml of benzyl chlorocarbonate and a further 1,050 ml of 1N NaOH were added dropwise simultaneously. The mixture was then stirred at room temperature for 2 hours, then extracted three times with ether and acidified with concentrated HCl to pH 1. The oil which separated out was extracted into ethyl acetate. The ethyl acetate solution was washed with water until the water phase had a pH of 3. After drying, the product crystallized on evaporation and scratching. 1.5 liters of diisopropyl ether were added and the mixture was stirred at room temperature for one hour. The product was then filtered off with suction; melting point 138°-139°.

Workup

  1. extractionextracted three times with ether
  2. customThe oil which separated out
  3. extractionwas extracted into ethyl acetate
  4. washThe ethyl acetate solution was washed with water until the water phase
  5. customAfter drying
  6. customthe product crystallized on evaporation
  7. addition1.5 liters of diisopropyl ether were added
  8. stirringthe mixture was stirred at room temperature for one hour
  9. filtrationThe product was then filtered off with suction

Sources & evidence

ORD record
ord-9f325789e8f34599b6c69c29383d298a
Source dataset
uspto-grants-1986_11
Patent number
US04624962

Reaction notes

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