反应详情

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%).

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