Triethylamine → (7-Benzyloxy-3-nitro-quinolin-4-yl)[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]amine

HRID 2383215Notes

Reaction equation

HRID 2383215 reaction equation
C(N(CC)CC)C.[CH2:8]([O:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20](Cl)=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[N:23]2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:30][C:31]1([CH3:38])[O:35][CH:34]([CH2:36][NH2:37])[CH2:33][O:32]1>ClCCl>[CH2:8]([O:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:37][CH2:36][CH:34]3[CH2:33][O:32][C:31]([CH3:38])([CH3:30])[O:35]3)=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[N:23]2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 41223491,3-Dioxolane-4-methanamine, 2,2-dimethyl-HCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 67051130(7-Benzyloxy-3-nitro-quinolin-4-yl)[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]amineYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (31.88 mL, 228.77 mmol, 1.5 eq) was added to a solution of 7-benzyloxy-4-chloro-3-nitroquinoline (48.00 g, 152.51 mmol, 1 eq) in dichloromethane (400 mL). Dropwise addition of 2,2-dimethyl-1,3-dioxolan-4-methanamine (20.0 g, 152.51 mmol, 1 eq) to the reaction mixture followed, which was then stirred at ambient temperature for 6 hours. The crude reaction mixture was concentrated under reduced pressure, and the resulting solid was triturated with water and then stirred for 1 hour. The precipitate was collected by filtration, washed with water, dried, suspended in diethyl ether (400 mL), sonicated, and the resulting precipitate material was collected by filtration. The product was dried under vacuum at 40° C. for 12 hours to afford 60.1 g of (7-benzyloxy-3-nitro-quinolin-4-yl)[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]amine as a yellow solid, mp 154-155° C. 1H-NMR (300 MHz, CDCl3) δ 9.74-9.62 (br m, 1H), 9.32 (s, 1H), 8.15 (d, J=9.4 Hz, 1H), 7.51-7.31 (m, 6H), 7.15 (dd, J=9.4, 2.7 Hz, 1H), 5.21 (s, 2H), 4.48-4.37 (m, 1H), 4.16-4.05 (m, 2H), 4.04-3.93 (m, 1H), 3.74 (dd, J=8.5, 5.9 Hz, 1H), 1.54 (s, 3H), 1.40 (s, 3H); MS (APCI) m/z 410.1 (M+H)+.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customthe resulting solid was triturated with water
  4. stirringstirred for 1 hour
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried
  8. customsonicated
  9. filtrationthe resulting precipitate material was collected by filtration
  10. customThe product was dried under vacuum at 40° C. for 12 hours

Sources & evidence

ORD record
ord-da7cf43bad704209a12b19ae4e3a7d89
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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