Hydrochloric Acid → HCID 14620978, compound

HRID 359460Notes

Reaction equation

HRID 359460 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][C:7](C)(C)[CH2:8][CH2:9][C:10]=2[CH:11]=1.[Li]CCCC.[CH3:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(#N)C1C=CC=CC=1.[ClH:33].C1C[O:37][CH2:36]C1>>[ClH:33].[C:36]([CH:6]1[C:5]2[N:4]=[CH:3][C:2]([CH3:1])=[CH:11][C:10]=2[CH2:9][CH2:8][CH2:7]1)(=[O:37])[C:21]1[CH:20]=[CH:19][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 7505BenzonitrileHCID 8028TetrahydrofuranHCID 122782055,6,7,8-Tetrahydro-3,7,7-trimethylquinolineHCID 178418244HCID 178418244, compound

Product 1

HCID 14620978HCID 14620978, compound

Procedure

To a solution of 5,6,7,8-tetrahydro-3-methylquinoline (3g) in THF (20ml) at 0° C under nitrogen was added 1.7 molar n-BuLi/hexane solution (12ml) followed by benzonitrile (2ml). The mixture was stirred at ambient temperature 1/2h then 2N HCl was added and the mixture was stirred a further 15 min. The aqueous layer was separated and washed with ether then basified and extracted with chloroform. The extracts were dried (MgSO4) and evaporated. The product was purified by chromatography, first on fluorisil with chloroform and them on silica with 2% MeOH/CHCl3 as eluant. The product was converted into the hydrochloride in propan-2-ol with a Et2O/HCl solution and allowed to crystallise to give 8-benzoyl-5,6,7,8-tetrahydro-3-methylquinoline hydrochloride (1.5g) m.p. 137°-40° C. (Found: C, 70.7; H, 6.5; N, 4.8. C17H17NO.HCl requires C, 70.95; H, 6.3; N, 4.9%.

Workup

  1. customThe aqueous layer was separated
  2. washwashed with ether
  3. extractionextracted with chloroform
  4. dry with materialThe extracts were dried (MgSO4)
  5. customevaporated
  6. customThe product was purified by chromatography, first on fluorisil with chloroform and them on silica with 2% MeOH/CHCl3 as eluant
  7. customto crystallise

Sources & evidence

ORD record
ord-6b56bca836a74c548d67301bd7a8d352
Source dataset
uspto-grants-1991_03
Patent number
US05001131

Reaction notes

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