Ethyl chloroformate → HCID 13117124, compound

HRID 1583382Notes

Reaction equation

HRID 1583382 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-63cbd69ea9e1490bbb2a09a42bb2ab92
Source dataset
uspto-grants-1985_11
Patent number
US04551474

Reaction notes

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