Ammonia → 6-Hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

HRID 48107

반응식

HRID 48107 반응식
N.[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([OH:15])=[O:14])[CH:7]=[CH:6]2.[Na].[Cl-].[NH4+]>C(O)C>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([C:13]([OH:15])=[O:14])[CH2:7][CH2:6]2

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 855576-Hydroxy-2-naphthoic acidHCID 5360545Sodium

생성물 1

HCID 190700016-Hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid수율 73%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Liquid ammonia (7 equi.) is condensed into a solution of 6-hydroxy-naphthalene-2-carboxylic acid (15) (1 equi) in ethanol (1.2 mL/mmole) at −78 C. Sodium (4.3 equi.) was added in 4 portions to the reaction mixture. Each portion gave blue color, but it disappeared quickly. The reaction mixture was stirred for 20 min, ammonium chloride (4.3 equi.) was added, it was stirred for another 1 h and anmmonia was distilled off by warming reaction pot to room temperature. The reaction mixture was quenched with water and 10% hydrochloric acid, extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by recrystallization from acetonitrile gave 6-hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (29) as a white solid (73%).

후처리

  1. customEach portion gave blue color, but it
  2. stirringit was stirred for another 1 h
  3. distillationanmmonia was distilled off
  4. temperatureby warming
  5. customreaction pot to room temperature
  6. customThe reaction mixture was quenched with water and 10% hydrochloric acid
  7. extractionextracted with ethyl acetate
  8. washwashed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customPurification
  12. customby recrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-578e310822384e5fa0018500ebdc105e
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703082B1

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