Ethyl chloroformate → HCID 68139532, compound

HRID 1288117Notes

Reaction equation

HRID 1288117 reaction equation
[CH3:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][C:3]=12.[Cl:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[OH-].[Na+]>C1C=CC=CC=1>[ClH:17].[CH2:21]([O:20][C:18]([N:14]1[CH2:15][CH2:16][C:3]2[C:4](=[N:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]=2[CH3:1])[CH2:12][CH2:13]1)=[O:19])[CH3:22]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 304399911-methyl-2,3,4,5-tetrahydro-1H-azepino[4,5-b]quinoline

Product 1

HCID 68139532HCID 68139532, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

11 gm (51.7 millimols) of 1,2,4,5-tetrahydro-11-methyl-3H-azepino[4,5-b]quinoline were dissolved in 275 ml of hot benzene, and then a solution of 9.8 ml (103.4 millimols) of ethyl chloroformate in 70 ml of benzene were simultaneously added dropwise. After refluxing the resulting mixture for 2 hours, 150 ml of ice water were added to the cooled reaction mixture, and the aqueous mixture was made alkaline with 2 N sodium hydroxide. The benzene layer was separated and the aqueous layer was extracted with chloroform. The combined benzene and chloroform phases were dried over sodium sulfate, the solvents were distilled off, and the residual oil was admixed with ether, whereupon 11 gm (75% of theory) of the base, m. p. 126° C., crystallized out. For conversion into the hydrochloride, 11 gm of the base were dissolved in 60 ml of isopropanol, the solution was filtered, and 10 ml of isopropanolic hydrochloric acid were added. The hydrochloride crystallized out of the hot solution. Yield: 12 gm (72% of theory); m.p. 247° C. (decomp.).

Workup

  1. temperatureAfter refluxing the resulting mixture for 2 hours
  2. customThe benzene layer was separated
  3. extractionthe aqueous layer was extracted with chloroform
  4. dry with materialThe combined benzene and chloroform phases were dried over sodium sulfate
  5. distillationthe solvents were distilled off
  6. customcrystallized out
  7. dissolutionFor conversion into the hydrochloride, 11 gm of the base were dissolved in 60 ml of isopropanol
  8. filtrationthe solution was filtered
  9. addition10 ml of isopropanolic hydrochloric acid were added
  10. customThe hydrochloride crystallized out of the hot solution

Sources & evidence

ORD record
ord-6573c4694f9147b586d78b2777dded98
Source dataset
uspto-grants-1976_10
Patent number
US03987047

Reaction notes

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