Hydrochloric Acid → 4-(cis-1,2,3,6-Tetrahydrophthalimidoethyl)aniline

HRID 35799

反応式

HRID 35799 の反応式
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][NH2:10])=[CH:6][CH:5]=1)([O-])=O.[C:13]1(=O)[O:18][C:16](=[O:17])[C@H:15]2[CH2:19][CH:20]=[CH:21][CH2:22][C@@H:14]12.Cl.[OH-].[NH4+]>C1(C)C=CC=CC=1.O>[C:13]1(=[O:18])[N:10]([CH2:9][CH2:8][C:7]2[CH:11]=[CH:12][C:4]([NH2:1])=[CH:5][CH:6]=2)[C:16](=[O:17])[C@H:15]2[CH2:19][CH:20]=[CH:21][CH2:22][C@@H:14]12

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14923Ammonium Hydroxide2 回HCID 951534-NitrophenethylamineHCID 98495Tetrahydrophthalic anhydride, cis-

生成物 1

HCID 677885684-(cis-1,2,3,6-Tetrahydrophthalimidoethyl)aniline

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

16.6 g of p-nitrophenethylamine and 15.1 g of cis-1,2,3,6-tetrahydrophthalic anhydride are heated under reflux in 300 ml of toluene, with stirring and a water trap, for 16 hours. This mixture is cooled and take to dryness by warming under reduced pressure. The residue is transferred to a flask containing 500 ml of water, 270 g ferrous sulfate heptahydrate and 1.3 ml concentrated hydrochloric acid. Steam is delivered to the mixture. When the temperature reaches 90° C., 75 ml of concentrated ammonium hydroxide is added in one portion, and at two-minute intervals three 25 ml portions of ammonium hydroxide are added. Continue stirring and heating during the additions. The total reaction time is 8-10 minutes. Immediately pour the mixture onto 1 kg of cracked ice. The solid is collected by filtration and washed with water. Recrystallize from water ethanol to obtain -4-(cis-1,2,3,6-tetrahydrophthalimidoethyl) aniline (1f).

後処理

  1. temperatureThis mixture is cooled
  2. temperatureby warming under reduced pressure
  3. customThe residue is transferred to a flask
  4. customreaches 90° C.
  5. stirringContinue stirring
  6. temperatureheating during the additions
  7. waitThe total reaction time is 8-10 minutes
  8. filtrationThe solid is collected by filtration
  9. washwashed with water
  10. customRecrystallize from water ethanol

出典と根拠

ORDレコード
ord-98f7a069146144aa925bada386f810db
出典データセット
uspto-grants-1995_05
特許番号
US05411869

関連ノート

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