Sodium Hydroxide → 4-[[(E)-(1-benzylindol-3-yl)methylideneamino]oxymethyl]-2-bromobenzoic acid

HRID 1392270노트

반응식

HRID 1392270 반응식
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11]/[N:12]=[CH:13]/[C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:15]=2)=[CH:6][C:5]=1[Br:30].[OH-].[Na+]>>[CH2:23]([N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](/[CH:13]=[N:12]/[O:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:31])=[O:2])=[C:5]([Br:30])[CH:6]=2)=[CH:15]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

3

반응물 2

HCID 14798Sodium HydroxideHCID 87730327HCID 87730327, 화합물

생성물 1

HCID 115762814-[[(E)-(1-benzylindol-3-yl)methylideneamino]oxymethyl]-2-bromobenzoic acid수율 77.1%

실험 절차

To a solution of 4-[({[(1E)-(1-benzyl-1H-indol-3-yl)methylidene]amino}oxy)methyl]-2-bromobenzoic acid methyl ester (0.20 g, 0.42 mmol) in 10/5/3 tetrahydrofuran/ethanol/water (12 mL) was added 2.5 M sodium hydroxide solution (2 mL). This mixture was heated to reflux for 3 hours and then allowed to cool back to room temperature. The mixture was concentrated to approximately ¼ volume and partitioned between ethyl acetate and water. The aqueous layer was acidified to approximately pH 1 using 1 N hydrochloric acid. The layers were then separated. The aqueous layer was extracted with one additional portion of ethyl acetate. The organics were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was recrystallized one time from ethyl acetate/hexanes (1/10) to give the title compound (0.15 g, 75%) as a white powder. mp=107-109° C. 1H NMR (400 MHz, DMSO-d6); δ 13.33 (bs, 1H), 8.42 (s, 1H), 7.92 (s, 1H), 7.90 (d, 1H), 7.73 (d, 1H), 7.71 (s, 1H), 7.52 (d, 1H), 7.44 (d, 1H), 7.23 (m, 7H), 5.52 (s, 2H), 5.28 (s, 2H). Mass spec; (ES+) m/z 462.9, (ES−) m/z 463.2. Elemental analysis; Calculated for C24H19BrN2O3: C, 62.22; H, 4.13; N, 6.05. Found: C, 61.61; H, 4.03; N, 5.82.

후처리

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationThe mixture was concentrated to approximately ¼ volume
  4. custompartitioned between ethyl acetate and water
  5. customThe layers were then separated
  6. extractionThe aqueous layer was extracted with one additional portion of ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was recrystallized one time from ethyl acetate/hexanes (1/10)

출처 및 근거

ORD 기록
ord-e2ec56ee8646415f9e2b685465b2fe7b
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342039B2

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