Hydrochloric Acid → Oxanilic acid

HRID 1968426노트

반응식

HRID 1968426 반응식
[C:1]([O:12]CC)(=[O:11])[C:2]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[OH-].[Na+].Cl.C(OCC)(=O)C>C1COCC1>[C:5]1([NH:4][C:2](=[O:3])[C:1]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 73826Ethyl oxanilate

생성물 1

HCID 10378Oxanilic acid수율 83.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl oxanilate 83 (Aldrich, 1.0 g, 1.0 eq) in 12 mL of THF was treated dropwise with a 1N NaOH solution (5.70 mL, 1.1 eq) resulting in a white precipitate. After stirring for 3 hours at RT, 0.5N HCl and ethyl acetate were added, the organic layer separated, washed with 0.5N HCl and brine and then dried over sodium sulfate, filtered, and concentrated to give 712 mg (68%) of N-phenyl oxalamic acid 84 as a white solid with consistent analytical data. FIA M+H=166.0, M−H=163.9; 1H NMR (DMSO-d6) δ 10.70 (s, 1H), 7.75 (m, 2H), 7.35 (m, 2H), 7.15 (m, 1H) ppm.

후처리

  1. customresulting in a white precipitate
  2. customthe organic layer separated
  3. washwashed with 0.5N HCl and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e5c552b149d041ac8a579b2f6dbdb3ad
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426359B2

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