Triethylamine → 4-butoxy-N-quinolin-3-yl-benzamide

HRID 1944514Notes

Reaction equation

HRID 1944514 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].CCN(CC)CC.[NH2:22][C:23]1[CH:24]=[N:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2>C(#N)C>[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH:22][C:23]2[CH:24]=[N:25][C:26]3[C:31]([CH:32]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 113753-AminoquinolineHCID 1185614-Butoxybenzoyl chloride

Product 1

HCID 104712524-butoxy-N-quinolin-3-yl-benzamideYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Butoxy-benzoyl chloride (0.21 mL, 1.11 mmol), Et3N (0.16 mL, 1.15 mL) and 3-aminoquinoline (0.153 g, 1.06 mmol) were stirred together in 10 mL acetonitrile in a round bottom flask for 4 hours. The reaction mixture was then evaporated in vacuo and the residue was triturated with 5 mL acetonitrile. The resulting solid was collected by filtration, rinsed with acetonitrile and dried to yield the title product as a cream-colored powder (0.284 g, 0.89 mmol). 1H NMR (CDCl3): δ 8.91 (s, 2H), 8.20 (s, 1H), 8.08 (d, 1H), 7.94 (d, 2H), 7.84 (d, 1H), 7.67 (t, 1H), 7.57 (t, 1H), 7.01 (d, 2H), 4.05 (t, 2H), 1.83 (p, 2H), 1.52 (h, 2H), 1.01 (t, 3H); MS: m/z 321.0 (MH+).

Workup

  1. customThe reaction mixture was then evaporated in vacuo
  2. customthe residue was triturated with 5 mL acetonitrile
  3. filtrationThe resulting solid was collected by filtration
  4. washrinsed with acetonitrile
  5. customdried

Sources & evidence

ORD record
ord-d937c47bcad34df1b7d255e8c71a6229
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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