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

HRID 2370786

반응식

HRID 2370786 반응식
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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 7853AllylamineHCID 11089Trimellitic anhydride

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

To a 25 mL pear-shaped flask was added solid 1,3-dioxo-1,3-dihydro-isobenzofuran-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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7b9e4b49b07f474682e023a335402950
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710043B2

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