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

HRID 2232539

反応式

HRID 2232539 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-718be82b29314e4eb59ec196f96c8a45
出典データセット
uspto-grants-1988_11
特許番号
US04788204

関連ノート

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