Phosphorus oxychloride → Methyl 2-(4-(cyclohex-1-enecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 1801356Notes

Reaction equation

HRID 1801356 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][CH:3]=1.[C:24]1([C:30](O)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=1.C(N(CC)C(C)C)(C)C.P(Cl)(Cl)(Cl)=O>ClCCl>[C:24]1([C:30]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH:8]3[C:17]([CH3:18])([CH3:19])[CH2:16][C:15]4[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=4)[NH:9]3)=[CH:6][CH:7]=2)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=1

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 694701-Cyclohexene-1-carboxylic acidHCID 81531DiisopropylethylamineHCID 67441380Methyl 2-(4-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 67441989Methyl 2-(4-(cyclohex-1-enecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(4-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (150 mg, 0.48 mmol), cyclohex-1-enecarboxylic acid (73 mg, 0.58 mmol) and N,N-diisopropylethylamine (0.2 mL, 1.2 mmol,) in dichloromethane (5 mL) was added phosphorus oxychloride (0.06 mL, 0.58 mmol) via syringe below 0° C. The mixture was stirred at room temperature for 16 hrs under nitrogen. The solvent was removed and the residue was washed with dichloromethane/petroleum ether, the precipitate was collected to afford methyl 2-(4-(cyclohex-1-enecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a yellow solid, 130 mg, yield: 60%.

Workup

  1. customThe solvent was removed
  2. washthe residue was washed with dichloromethane/petroleum ether
  3. customthe precipitate was collected

Sources & evidence

ORD record
ord-c6d6a12f6a384d65859ee35e04c3f4c8
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

Loading…