Lithium Hydroxide → 2-Cyanoisonicotinic Acid

HRID 1397283

반응식

HRID 1397283 반응식
[OH-].[Li+].[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][N:14]=1)[C:8]([O:10]C)=[O:9])#[N:4]>C1COCC1.O>[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][N:14]=1)[C:8]([OH:10])=[O:9])#[N:4]

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 12132796Methyl 2-cyanopyridine-4-carboxylate

생성물 1

HCID 27625132-Cyanoisonicotinic Acid수율 89.4%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

Lithium hydroxide (96 mg, 4.0 mmol) was added to a solution of methyl 2-cyanoisonicotinate (0.6 g, 3.7 mmol) in THF—H2O (20 mL, 7:3 v/v) at 0° C. The reaction mixture was allowed to warm up to room temperature and further stirred for 1 h. The reaction mixture was concentrated under reduced pressure and then diluted with water. The aqueous layer was washed with EtOAc. The pH of the aqueous layer was adjusted to ˜3 using 1.5N HCl and the organic product was extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 2-cyanoisonicotinic acid (490 mg, yield 89%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 14.11 (br s, 1H), 8.93-8.91 (dd, J=4.9 Hz, 0.8 Hz, 1H), 8.34 (d, J=0.9 Hz, 1H), 8.11-8.10 (m, 1H). MS (ESI) m/z: Calculated for C7H4N2O2: 148.03. found: 147.2 (M−H)−.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. washThe aqueous layer was washed with EtOAc
  4. extractionthe organic product was extracted with EtOAc
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-dcecbd1d3e0b4f81b76838f2d5847a74
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901156B2

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