1-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methanamine → HCID 68817756, compound

HRID 9483Notes

Reaction equation

HRID 9483 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:16][C:17]1([CH3:24])[O:21][C@H:20]([CH2:22][NH2:23])[CH2:19][O:18]1>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:23][CH2:22][C@@H:20]3[CH2:19][O:18][C:17]([CH3:24])([CH3:16])[O:21]3)=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 101540731-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methanamineHCID 219843617-Bromo-4-chloro-3-nitroquinoline

Product 1

HCID 68817756HCID 68817756, compoundYield 88.4%

Procedure

7-Bromo-4-chloro-3-nitroquinoline (22.00 g, 76.52 mmol) was treated with (R)-2,2-dimethyl-1,3-dioxolane-4-methanamine (11.61 g, 114.8 mmol) according to the method described in Part A of Examples 152–156. The crude product was triturated with water (200 mL), isolated by filtration, washed with water, dried, and suspended in diethyl ether (100 mL). The suspension was sonicated, and the resulting solid was isolated by filtration, and dried for four hours in a vacuum oven at 40° C. to provide 25.84 g of (R)-(7-bromo-3-nitroquinolin-4-yl)-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)amine as a yellow solid, mp 136–137° C.

Workup

  1. customThe crude product was triturated with water (200 mL)
  2. customisolated by filtration
  3. washwashed with water
  4. customdried
  5. customThe suspension was sonicated
  6. customthe resulting solid was isolated by filtration
  7. customdried for four hours in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-6ce4ecf087dd4b5e9dfdb947815f2d30
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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