Triethylamine → 4-chloro-N,N-bis(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide

HRID 44407Notes

Reaction equation

HRID 44407 reaction equation
C(N(CC)CC)C.P(Cl)(Cl)([Cl:10])=O.O[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][C:16](=[O:24])[C:15]=1[C:25]([N:27]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[O:26]>>[Cl:10][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][C:16](=[O:24])[C:15]=1[C:25]([N:27]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[O:26]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 670981304-hydroxy-N,N-bis(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide

Product 1

HCID 670975844-chloro-N,N-bis(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxamideYield 67%

Conditions

Temperature
65 °C

Procedure

Triethylamine (5.73 mL, 41.2 mmol) was added to phosphorus oxychloride (60 mL), followed by 4-hydroxy-N,N-bis(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide (Example 74c) (6.11 g, 13.7 mmol). The reaction was heated at 65° C. for 4 hours, then cooled to room temperature and carefully poured into ice water (1200 mL). The solution was extracted dichloromethane (2×200 mL. The organic layers were combined and washed with water, dried over MgSO4, filtered and evaporated. The residue was dissolved in dichloromethane (18 mL) and poured into 200 mL of 30% hexanes in diethyl ether. The resultant precipitate was collected by filtration to give crude 4-chloro-N,N-bis(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide (4.25 g, 67%) which was used without further purification. MS 463 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe solution was extracted dichloromethane (2×200 mL
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue was dissolved in dichloromethane (18 mL)
  8. additionpoured into 200 mL of 30% hexanes in diethyl ether
  9. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-37508290e5a94d8db4002b834847f503
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Reaction notes

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