Hydrochloric Acid → Oxanilic acid

HRID 1968426ノート

反応式

HRID 1968426 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 10378Oxanilic acid収率 83.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e5c552b149d041ac8a579b2f6dbdb3ad
出典データセット
uspto-grants-2013_04
特許番号
US08426359B2

反応ノート

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