4-Nitrobenzoyl chloride → HCID 4148717, compound

HRID 1249534Notes

Reaction equation

HRID 1249534 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:13]1([NH2:23])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1>O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH:23][CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 180661,2,3,4-Tetrahydro-1-naphthylamine

Product 1

HCID 4148717HCID 4148717, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 11430Potassium CarbonateSolvent

Procedure

A solution of 18.9 g of 4-nitrobenzoyl chloride in 100 ml of tetrahydrofuran was added rapidly to a solution of 10.0 g of 1,2,3,4-tetrahydro-1-naphthylamine in 200 ml of tetrahydrofuran and 180 ml of 20% aqueous potassium carbonate. The reaction mixture was stirred vigorously and heated at reflux for 2 hours. After cooling, the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic portions were washed with water, 1N hydrochloric acid, water, and a saturated sodium chloride solution, dried over sodium sulfate, and concentrated in vacuo. The resulting solid was recrystallized from benzene to afford the title intermediate in 90% yield as a colorless solid, m.p. 156°-157° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic portions were washed with water, 1N hydrochloric acid, water
  7. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe resulting solid was recrystallized from benzene

Sources & evidence

ORD record
ord-ba80e0abe23840269952bb0244cddf36
Source dataset
uspto-grants-1986_12
Patent number
US04632939

Reaction notes

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