Dimethylformamide → 9-Formyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene-4-carboxylic Acid Methyl Ester

HRID 2415792노트

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HRID 2415792 반응식
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:20])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][CH:17]=[O:18])[C:11]=1[OH:19].CN(C=O)C.Br[CH2:27][CH2:28][CH2:29]Cl>O.C(OCC)(=O)C>[CH3:7][O:8][C:9]([C:10]1[C:11]2[O:19][CH2:29][CH2:28][CH2:27][N:16]([CH:17]=[O:18])[C:12]=2[CH:13]=[CH:14][CH:15]=1)=[O:20]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate2회HCID 167564653-Formylamino-2-hydroxy-benzoic Acid Methyl Ester

생성물 1

HCID 865900309-Formyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene-4-carboxylic Acid Methyl Ester수율 75.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

Potassium carbonate was ground and flame dried prior to each use. 3-formylamino-2-hydroxy-benzoic acid methyl ester compound (1.952 grams, 10 mmol) and potassium carbonate (2.764 grams, 20 mmol, 2 eq.) were placed in a flask together with 100 mL of anhydrous DMF. Heated to 120° C. for 1 hour. 1-bromo-3-chloropropane (1 mL, 10 mmol, 1 eq.) was added to the reaction mixture in several portions at 120° C. and the reaction heated for an additional 3 hours. The reaction was monitored on TLC (ethyl acetate). After cooling, the reaction mixture was stripped to a minimal volume, diluted with water and extracted three times with ethyl acetate. The combined organic portions were washed with water, brine and dried over magnesium sulfate. Filtration and solvent removal afforded crude product as a thick brown syrup (1.78 grams) which was chromatographed on silica gel using 30% ethyl acetate in hexane as eluent. The product was obtained in 67% yield as light yellow solid. M+236.

후처리

  1. temperatureflame
  2. customdried
  3. temperaturethe reaction heated for an additional 3 hours
  4. temperatureAfter cooling
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic portions were washed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration and solvent removal

출처 및 근거

ORD 기록
ord-36f0ca6bd6b34b8bbda7772f42ca4ad5
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06821977B2

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