Water → Ethyl 2-(3-methoxyphenyl)-4-quinazolinepropionate

HRID 2232539

반응식

HRID 2232539 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=O.[NH2:12][C:13]1[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=1[C:15]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=O.C([N:30](CC)CC)C.O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[N:30]=[C:15]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]3[C:13](=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:12]=2)[CH:9]=[CH:10][CH:11]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 21283602Ethyl 4-(2-aminophenyl)-4-oxobutanoate

생성물 1

HCID 13769245Ethyl 2-(3-methoxyphenyl)-4-quinazolinepropionate

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

3-Methoxybenzoyl chloride (2.81 cc) is added at 5° C. to ethyl 3-(2-aminobenzoyl)propionate (2.21 g) and triethylamine (4.2 cc) in chloroform (25 cc). The mixture is left for 1 hour at room temperature (approximately 20° C.), water (25 cc) is added and the mixture decanted. The organic phase is evaporated under reduced pressure and the residue taken up with ammonium acetate (17 g). The mixture is brought to 100° C. for 7 hours and the acetic acid formed is then evaporated off under reduced pressure. The residue is poured into water (100 cc) and the aqueous phase extracted with ethyl acetate (3×50 cc). The aqueous phase is dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure. The residual product is chromatographed in silica gel with a cyclohexane/ethyl acetate (1:1 by volume) mixture as eluant. After recrystallization in ethanol, ethyl 2-(3-methoxyphenyl)-4-quinazolinepropionate (1.5 g), m.p. 70° C., is obtained.

후처리

  1. additionis added
  2. customthe mixture decanted
  3. customThe organic phase is evaporated under reduced pressure
  4. customthe acetic acid formed
  5. customis then evaporated off under reduced pressure
  6. additionThe residue is poured into water (100 cc)
  7. extractionthe aqueous phase extracted with ethyl acetate (3×50 cc)
  8. dry with materialThe aqueous phase is dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness under reduced pressure
  11. customThe residual product is chromatographed in silica gel with a cyclohexane/ethyl acetate (1:1 by volume) mixture as eluant
  12. customAfter recrystallization in ethanol

출처 및 근거

ORD 기록
ord-718be82b29314e4eb59ec196f96c8a45
출처 데이터셋
uspto-grants-1988_11
특허 번호
US04788204

연결된 노트

불러오는 중…