Acetic Acid → 5,6,7,8-Tetrahydro-N-phenyl-7-quinolinamine

HRID 1461290Notes

Reaction equation

HRID 1461290 reaction equation
C(O)(=O)C.[N:5]1[C:14]2[CH:13]=[CH:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[Na+].[OH-].[Na+]>CO.O>[C:16]1([NH:15][CH:12]2[CH2:13][C:14]3[N:5]=[CH:6][CH:7]=[CH:8][C:9]=3[CH2:10][CH2:11]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 6115AnilineHCID 14798Sodium HydroxideHCID 123183175,6-Dihydroquinoline

Product 1

HCID 148359785,6,7,8-Tetrahydro-N-phenyl-7-quinolinamineYield 66.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Glacial acetic acid (1.2 ml, 20 mmol) was added dropwise to a stirred solution of 5,6-dihydroquinoline (1.31 g, 10 mmol) and aniline (1.86 g, 20 mmol) in methanol (4 ml). The solution was heated under reflux for 21h, cooled to room temperature, poured onto a mixture of saturated aqueous sodium chloride (25 ml) and water (25 ml), and the mixture was basified with 10N-NaOH and extracted with ether (3×25 ml). The extracts were concentrated in vacuo to give a dark orange oil which was chromatographed [alumina; ethyl acetate-toluene (1:24 to 1:4)] to give a solid. Recrystallisation from di-isopropyl ether gave the product (1.50 g), mp 102°-103°. (Found: C, 80.4; H, 76.2; N, 12.5. C15H16N2 requires C, 80.3; H, 7.2; N, 12.5%)

Workup

  1. temperatureThe solution was heated
  2. extractionextracted with ether (3×25 ml)
  3. concentrationThe extracts were concentrated in vacuo
  4. customto give a dark orange oil which
  5. customwas chromatographed [alumina; ethyl acetate-toluene (1:24 to 1:4)]
  6. customto give a solid
  7. customRecrystallisation from di-isopropyl ether

Sources & evidence

ORD record
ord-a7c7e75926ed478883638c4cfb2763a7
Source dataset
uspto-grants-1991_12
Patent number
US05075303

Reaction notes

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