Sodium Hydroxide → 2-(Quinolin-6-yl)prop-2-enoic acid

HRID 1798914노트

반응식

HRID 1798914 반응식
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](=[CH2:16])[C:12]([O:14]C)=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCCC1.O>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](=[CH2:16])[C:12]([OH:14])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 67368576Methyl 2-(quinolin-6-yl)acrylate

생성물 1

HCID 219927482-(Quinolin-6-yl)prop-2-enoic acid수율 51.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Accordingly, as shown in step iii of Scheme 1, methyl 2-(quinolin-6-yl)acrylate (75.0 g) was dissolved in a solution containing sodium hydroxide (65.2 g, 1.63 mol) in 1.1 liters of tetrahydrofuran and 1.1 liters of water. The reaction was stirred at room temperature overnight. The organic layer was partitioned off and the aqueous layer washed with 500 mL of toluene. The aqueous layer was then cooled with an ice bath and acidified by dropwise addition of concentrated HCl until a pH of 4.5 was achieved (about 125 mL of conc. HCl, 1.508 mol), resulting in a white precipitate. After the addition was complete, the reaction was stirred for an additional 0.5 hour at 5° C. The precipitate was collected by vacuum filtration, washed with water, washed with methyl t-butyl ether, and dried under vacuum to afford 2-(quinolin-6-yl)acrylic acid (compound 1003, 36.2 g): ESMS (M+1), 200.06; 1H NMR (300.0 MHz, DMSO-d6) δ 13.01 (1H, s), 8.91 (1H, dd, J=1.8, 4.2 Hz), 8.40 (1H, d, J=7.5 Hz), 8.07 (1H, d, J=1.8 Hz), 8.01 (1H, d, J=8.7 Hz), 7.84 (1H, dd, J=1.9, 8.9 Hz), 7.55 (1H, dd, J=1.2, 8.4 Hz), 6.39 (1H, d, J=0.9 Hz), 6.17 (1H, d, J=0.9 Hz).

후처리

  1. dissolutionwas dissolved in a solution
  2. customThe organic layer was partitioned off
  3. washthe aqueous layer washed with 500 mL of toluene
  4. temperatureThe aqueous layer was then cooled with an ice bath
  5. additionacidified by dropwise addition of concentrated HCl until a pH of 4.5
  6. customresulting in a white precipitate
  7. additionAfter the addition
  8. stirringthe reaction was stirred for an additional 0.5 hour at 5° C
  9. filtrationThe precipitate was collected by vacuum filtration
  10. washwashed with water
  11. washwashed with methyl t-butyl ether
  12. customdried under vacuum

출처 및 근거

ORD 기록
ord-e5351451576f479b8704dc6b099f7d01
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343998B2

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