Dimethylcarbamoyl Chloride → 7-Methylquinoline-2-carbonitrile

HRID 2422533Notes

Reaction equation

HRID 2422533 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N+:9]2[O-])=[CH:4][CH:3]=1.C[Si]([C:17]#[N:18])(C)C.CN(C)C(Cl)=O>ClCCCl>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:17]#[N:18])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 232711687-Methylquinoline 1-oxide

Product 1

HCID 107971837-Methylquinoline-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 7-methylquinoline-1-oxide (18.3 g, 115 mmol) in 1,2-dichloroethane (750 mL) was added trimethylsilyl cyanide (30.8 mL, 230 mmol) followed by dimethylcarbamoyl chloride (21.2 mL, 230 mmol) and stirred at room temperature overnight. The solution was quenched slowly with a sat. solution of sodium bicarbonate, diluted with water and extracted two times with dichloromethane. The combined organic extracts were dried (MgSO4) and concentrated to give the crude compound. Flash chromatography of the residue on silica gel (eluting with 3% acetone in dichloromethane) provided the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.56 (d, 1H), 8.03 (d, 1H), 7.95 (s, 1H), 7.88 (d, 1H), 7.67 (d, 1H), 2.62 (s, 3H).

Workup

  1. customThe solution was quenched slowly with a sat. solution of sodium bicarbonate
  2. additiondiluted with water
  3. extractionextracted two times with dichloromethane
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customto give the crude compound

Sources & evidence

ORD record
ord-4fbeebecdd2e468f85942f43a97ea8ee
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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