Hydrochloric Acid → 1,3-dioxo-2-(prop-2-en-1-yl)-2,3-dihydro-1H-isoindole-5-carboxylic acid

HRID 509348

反応式

HRID 509348 の反応式
O=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[C:4](=[O:14])[O:3]1.[CH2:15]([NH2:18])[CH:16]=[CH2:17].C1(C)C=CC=CC=1.Cl>C(Cl)Cl.CC(O)=O>[CH2:15]([N:18]1[C:4](=[O:14])[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]([OH:13])=[O:12])[CH:6]=2)[C:2]1=[O:3])[CH:16]=[CH2:17]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 7853AllylamineHCID 11089Trimellitic anhydride

生成物 1

HCID 35075911,3-dioxo-2-(prop-2-en-1-yl)-2,3-dihydro-1H-isoindole-5-carboxylic acid

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

To a 25 mL pear-shaped flask was added solid 1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylic acid (200 mg, 1.041 mmol) and allylamine (234 μL, 3.12 mmol, 3 eq) via syringe. Toluene (2 mL) and AcOH (1 mL) were added via syringes and the flask was refluxed for 12 h. The flask was allowed to cool and then subjected to a DCM (75 mL) and HCl (1N, 50 mL) work up. The aqueous layer was extracted with DCM (3×25 mL). The combined organic layers were washed with brine, dried with sodium sulfate, filtered and concentrated. The residue thus obtained was azeotropically dried with toluene (2×, 5 mL) and heptane (2×5 mL). The resulting reside was placed on a high vacuum for 3 to give 2-allyl-1,3-dioxoisoindoline-5-carboxylic acid.

後処理

  1. temperaturethe flask was refluxed for 12 h
  2. temperatureto cool
  3. extractionThe aqueous layer was extracted with DCM (3×25 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue thus obtained
  9. dry with materialwas azeotropically dried with toluene (2×, 5 mL) and heptane (2×5 mL)

出典と根拠

ORDレコード
ord-656b9c6b87d149639cc3461162ac0922
出典データセット
uspto-grants-2015_08
特許番号
US09096527B2

関連ノート

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