Potassium Carbonate → (S)-N-(a-ethylbenzyl)-3-(cyanomethoxy)-2-phenylquinoline-4-carboxamide

HRID 651069

Reaction equation

HRID 651069 reaction equation
[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]=1[OH:29])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:37][C:38]#[N:39]>C1COCC1>[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]=1[O:29][CH2:37][C:38]#[N:39])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 5311424Talnetant

Product 1

HCID 54316707(S)-N-(a-ethylbenzyl)-3-(cyanomethoxy)-2-phenylquinoline-4-carboxamideYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g (5.23 mmol) of (S)-N-(α-ethylbenzyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (compound of Description 1), 2.21 g of K2CO3, 0.26 g (1.57 mmol) of KI and 0.52 ml (7.85 mmol) of bromoacetonitrile were stirred in 30 ml of dry THF for 5 hours. The inorganic salts were filtered off and the filtrate was evaporated in vacuo to dryness. The residue was dissolved in CH2Cl2 and the organic phase was washed with H2O, sat. sol. NaHCO3, sat. sol. NaCl, separated, dried over Na2SO4 and evaporated in vacuo to dryness to afford 2.10 g of a brown oil which was flash chromatographed on 230-400 mesh silica gel, eluting with a mixture of hexane/EtOAc 70:30. The crude product was triturated with hexane, filtered, washed and dried to yield 0.75 g of the title compound as a white solid.

Workup

  1. filtrationThe inorganic salts were filtered off
  2. customthe filtrate was evaporated in vacuo to dryness
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washthe organic phase was washed with H2O, sat. sol. NaHCO3, sat. sol. NaCl
  5. customseparated
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-95dae2f82a1d413f88ba57f8d055dba3
Source dataset
uspto-grants-2001_08
Patent number
US06277862B1

Linked notes

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