3-Hydroxyanthranilic Acid → Methyl 2-(4-chlorophenyl)benzoxazole-4-carboxylate

HRID 506235노트

반응식

HRID 506235 반응식
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:11].[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.[CH3:22]CN(C(C)C)C(C)C.CI>CN(C=O)C.C(OCC)(=O)C.Cl>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]2[O:1][C:2]3[C:3](=[C:4]([C:5]([OH:7])=[O:6])[CH:8]=[CH:9][CH:10]=3)[N:11]=2)=[CH:15][CH:14]=1.[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]2[O:18][C:2]3[C:3](=[C:4]([C:5]([O:7][CH3:22])=[O:6])[CH:8]=[CH:9][CH:10]=3)[N:11]=2)=[CH:15][CH:14]=1

참가 물질

9

반응물 4

HCID 863-Hydroxyanthranilic AcidHCID 6328Methyl iodideHCID 85014-Chlorobenzoyl chlorideHCID 81531Diisopropylethylamine

생성물 2

HCID 596258542-(4-Chlorophenyl)benzoxazole-4-carboxylic acidHCID 68459315Methyl 2-(4-chlorophenyl)benzoxazole-4-carboxylate수율 30%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

2-(4-Chlorophenyl)benzoxazole-4-carboxylic acid was prepared from 3-hydroxyanthranilic acid and 4-chlorobenzoyl chloride using the method described in Step A of Example 1. This crude material (2.90 g, 10.6 mmol) was directly dissolved in DMF (40 mL), DIPEA (5.46 g, 42.4 mmol) and methyl iodide (5.93 g, 42.4 mmol) added and the reaction stirred at room temperature for 18 h. After this time the reaction was diluted with ethyl acetate (100 mL) and 2 N HCl (50 mL). The organic layer was separated and then washed with 2 N HCl (25 mL), water (50 mL) and brine (50 mL). The organic layer was then dried over sodium sulfate, filtered and concentrated to dryness to yield light yellow oil. This material was purified using silica gel chromatography to afford 0.532 g (30% yield) of methyl 2-(4-chlorophenyl)benzoxazole-4-carboxylate as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.28 (dd, J=6.9, 1.8 Hz, 2H), 8.04 (d, J=8.1 Hz, 1H), 7.78 (d, J=8.1 Hz, 1H), 7.52 (d, J=8.7 Hz, 2H), 7.43 (t, J=7.8 Hz, 1H), 4.06 (s, 3H); MS (ESI) m/z 288 [M+H]+

후처리

  1. customThe organic layer was separated
  2. washwashed with 2 N HCl (25 mL), water (50 mL) and brine (50 mL)
  3. dry with materialThe organic layer was then dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customto yield light yellow oil
  7. customThis material was purified

출처 및 근거

ORD 기록
ord-b859a37d311a44c79c378c77da9715d0
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781430B2

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