Ethyl chloroformate → HCID 13117124, compound

HRID 354562Notes

Reaction equation

HRID 354562 reaction equation
C[N:2]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1.CCOCC>[CH2:26]([O:25][C:23]([N:2]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1)=[O:24])[CH3:27]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 13117105HCID 13117105, compound

Product 1

HCID 13117124HCID 13117124, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-methyl-4-(p-nitrophenoxy)-1,2,3,4-tetrahydroisoquinoline of Example 23 (6.0 g, 0.021 mole), ethyl chloroformate (2.9 g, 0.026 mole) and potassium carbonate (10 g) in benzene (100 ml) is refluxed for four hours. The reaction mixture is diluted with ether, washed with water, dilute HCl, again with water, then dried (saturated NaCl, anhydrous MgSO4). An analytical sample is twice recrystallized from hexanes/acetone (10:1) to yield 2-ethoxycarbonyl-4-(p-nitrophenoxy)-1,2,3,4-tetrahydroisoquinoline, m.p. 118°-119° C.

Workup

  1. temperatureis refluxed for four hours
  2. washwashed with water, dilute HCl, again with water
  3. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  4. customAn analytical sample is twice recrystallized from hexanes/acetone (10:1)

Sources & evidence

ORD record
ord-1a0c53fecf8a43d38e49d6bb22c1e707
Source dataset
uspto-grants-1983_03
Patent number
US04375471

Reaction notes

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