Hydrochloric Acid → 5,6,7,8-Tetrahydro-3-methyl-8-(4-nitrobenzamido) quinoline

HRID 359461Notes

Reaction equation

HRID 359461 reaction equation
[NH2:1][CH:2]1[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].CCOCC.Cl.Cl>C(Cl)Cl.C(N(CC)CC)C>[CH3:12][C:8]1[CH:9]=[N:10][C:11]2[CH:2]([NH:1][C:20](=[O:21])[C:19]3[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:24][CH:23]=3)[CH2:3][CH2:4][CH2:5][C:6]=2[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 10953452Ether hydrochlorideHCID 123582203-Methyl-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 146209795,6,7,8-Tetrahydro-3-methyl-8-(4-nitrobenzamido) quinoline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To 8-amino-5,6,7,8-tetrahydro-3-methylquinoline (4.5g, 2.27 M moles) in CH2Cl2 was added 4-nitrobenzoylchloride (4.2g, 2.26Mmoles) followed by sufficient triethylamine to clear the solution and then form a new precipitate. This material was left overnight and then the solvent removed. The residue was taken up in 2M HCl and washed with ethyl acetate. The aquous layer was then basified with Na2CO3 and extracted with chloroform. The organic solution was dried (MgSO4) and evaporated under reduced pressure to give a residue which was treated with Et2O/HCl to give a white solid identified by infra-red and nmr specroscopy as the hydrochloride of the title compound.

Workup

  1. customform a new precipitate
  2. customthe solvent removed
  3. washwashed with ethyl acetate
  4. extractionextracted with chloroform
  5. dry with materialThe organic solution was dried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto give a residue which
  8. customto give a white solid

Sources & evidence

ORD record
ord-85bf64d36df24e19b086bfe8a5bafa85
Source dataset
uspto-grants-1991_03
Patent number
US05001131

Reaction notes

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