Triethylamine → HCID 67690930, compound

HRID 484433Notes

Reaction equation

HRID 484433 reaction equation
Cl.[NH2:2][C@@H:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[CH:10][C:11]=2[Cl:13])[NH:6][C@@H:5]([C:15]([O:17][CH3:18])=[O:16])[CH2:4]1.C(N(CC)CC)C.[C:26](Cl)(=[O:30])[CH2:27][CH2:28][CH3:29]>ClCCl>[Cl:13][C:11]1[CH:10]=[C:9]([Cl:14])[CH:8]=[C:7]2[C:12]=1[C@@H:3]([NH:2][C:26]([CH2:27][CH2:28][CH3:29])=[O:30])[CH2:4][C@H:5]([C:15]([O:17][CH3:18])=[O:16])[NH:6]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 67690826HCID 67690826, compound

Product 1

HCID 67690930HCID 67690930, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of trans-4-amino-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline hydrochloride (example 9a) (0.200 g, 0.642 mmol) in anhydrous dichloromethane (15 ml) under an atmosphere of nitrogen was added dry triethylamine (0.197 ml, 1.41 mmol) and the mixture was stirred until dissolution was complete. To this solution was then added butyryl chloride (0.073 ml, 0.706 mmol) and the reaction was stirred at room temperature for 4 h. The mixture was then evaporated to dryness in vacuo and the residue was partitioned between ethyl acetate (50 ml) and 0.5M aqueous citric acid (30 ml). The organic layer was separated, washed successively with saturated sodium bicarbonate solution (1×30 ml) and brine (1×30 ml), then dried (MgSO4) and evaporated to give a solid which was triturated with diethyl ether. The solid was collected by filtration to give the pure title compound as colourless crystals (0.187 g), m.p. 205°-206° C. δ (CDCl3, 360 MHz) 0.96 (3H, t, J=7.4 Hz, COCH2CH2CH3). 1.64-1.72 (3H, m, CHACHBHCCHD and COCH2CH2CH3), 2.17 (2H, t, J=7.4 Hz, COCH2CH2CH3), 2.68 (1H, dm, J=14.0 Hz, CHACHBHCCHD), 3.81 (3H, s, CO2CH3), 3.94 (1H, dd, J= 12.6 and 2.9 Hz, CHACHBHCCHD), 4.85 (1H, br.s, ArNH), 5.26 (1H, m, CHACHBHCCHDNHCO), 5.37 (1H, br.d, J=18 7 Hz, CHDNHCO), 6.56 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.73 (1H, d, J=2.0 Hz, 6-H or 8-H). m/e (CI+) 345 (100%, (M+I)+).

Workup

  1. customThe mixture was then evaporated to dryness in vacuo
  2. customthe residue was partitioned between ethyl acetate (50 ml) and 0.5M aqueous citric acid (30 ml)
  3. customThe organic layer was separated
  4. washwashed successively with saturated sodium bicarbonate solution (1×30 ml) and brine (1×30 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a solid which
  8. customwas triturated with diethyl ether
  9. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-34cc88db88a44263a95d42ae3d086cb9
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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