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

HRID 2203558Notes

Reaction equation

HRID 2203558 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1([CH3:16])[O:13][CH:12]([CH2:14][NH2:15])[CH2:11][O:10]1.[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](Cl)=[C:30]([N+:35]([O-:37])=[O:36])[CH:31]=[N:32]2)=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl>[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([NH:15][CH2:14][CH:12]3[CH2:11][O:10][C:9]([CH3:16])([CH3:8])[O:13]3)=[C:30]([N+:35]([O-:37])=[O:36])[CH:31]=[N:32]2)=[CH:27][CH:26]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=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) followed by 2,2-dimethyl-1,3-dioxolan-4-methanamine (20.0 g, 152.51 mmol) were added to a solution of 7-benzyloxy-4-chloro-3-nitroquinoline (48.00 g, 152.51 mmol) in dichloromethane (400 mL), which was then stirred at ambient temperature for 6 hours. The crude reaction mixture was concentrated under reduced pressure, and the resulting solid was treated with water. The mixture was stirred for 1 hour. The solid 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.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. additionthe resulting solid was treated with water
  4. stirringThe mixture was stirred for 1 hour
  5. filtrationThe solid 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-5883e65dd3034f049a762908c792b7cf
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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