Methyl 4-aminobenzoate → Methyl 4-[(1,1-dimethyl-3-phenyl-1H-indene-5-carbonyl)amino]benzoate

HRID 265441노트

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HRID 265441 반응식
[CH3:1][C:2]1([CH3:21])[C:10]2[C:5](=[CH:6][C:7]([C:11](OC)=[O:12])=[CH:8][CH:9]=2)[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3]1.[OH-].[Na+].C(Cl)(=O)C(Cl)=O.[NH2:30][C:31]1[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=1>CO.O1CCCC1.CN(C)C=O.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:21])[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:39][CH:40]=3)=[O:12])=[CH:8][CH:9]=2)[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3]1

참가 물질

9

반응물 4

HCID 12082Methyl 4-aminobenzoateHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 19034436Methyl 1,1-dimethyl-3-phenyl-1H-indene-5-carboxylate

생성물 1

HCID 19034396Methyl 4-[(1,1-dimethyl-3-phenyl-1H-indene-5-carbonyl)amino]benzoate수율 85%

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 887Methanol용매HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Methyl 1,1-dimethyl-3-phenyl-1H-indene-5-carboxylate (315 mg, 1.13 mmol) was stirred with 10N NaOH (1.1 mL, 11.0 mmol) in 5 mL of methanol and 10 mL of tetrahydrofuran at 60° C. for 1.5 hours. The solution was concentrated under reduced pressure and acidified with 1N HCl (15 mL), extracted with ethyl acetate (15 mL×3). The combined extracts were washed with water (10 mL), dried over magnesium sulfate, and evaporated. The residue was dried in vacuum and dissolved in 2.5 mL of methylene chloride. To the solution was added oxalyl chloride (348 mg, 2.74 mmol) and 2 drops of dimethylformamide at 0° C. The solution was stirred at 0° C. for 30 min and at room temperature for 30 min. The mixture was evaporated and dried in vacuum. The residue was stirred with methyl 4-aminobenzoate (181 mg, 1.32 mmol) in 2 mL of anhydrous pyridine for 18 hours. Excess pyridine was evaporated and the residue was diluted with 20 mL of 2N HCl, extracted with ethyl ether (30 mL×4). The combined extracts were washed with water (10 mL), dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (EtOAc:hexane=1:20 to 1:5) to give 372 mg (85% yield) of the title compound as a glassy mass; 1H-NMR (CDCl3) δ 1.43 (s, 6H), 3.91 (s, 3H), 6.52 (s, 1H), 7.40-7.50 (m, 4H), 7.59-7.61 (m, 2H), 7.72-7.75 (m, 3H), 7.96 (s, 1H), 8.00 (bs, 1H), 8.05 (d, J=8.7 Hz, 2H); MS m/e 398 (MH+).

후처리

  1. concentrationThe solution was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate (15 mL×3)
  3. washThe combined extracts were washed with water (10 mL)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was dried in vacuum
  7. dissolutiondissolved in 2.5 mL of methylene chloride
  8. customThe mixture was evaporated
  9. customdried in vacuum
  10. customExcess pyridine was evaporated
  11. additionthe residue was diluted with 20 mL of 2N HCl
  12. extractionextracted with ethyl ether (30 mL×4)
  13. washThe combined extracts were washed with water (10 mL)
  14. dry with materialdried over magnesium sulfate
  15. customevaporated
  16. customThe residue was purified by flash chromatography (EtOAc:hexane=1:20 to 1:5)

출처 및 근거

ORD 기록
ord-2f8251453c4b490e800c1051e8ad1d24
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648385

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