Sodium Hydroxide → HCID 13054533, compound

HRID 1762044Notes

Reaction equation

HRID 1762044 reaction equation
Cl.[NH2:2][CH:3]1[CH:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.[OH-].[Na+]>O>[NH2:2][CH:3]1[CH:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23050707HCID 23050707, compound

Product 1

HCID 13054533HCID 13054533, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.3 Parts of a syn-anti-mixture of 9-oximino-1,2,3,4,4a,9,9a,10-octahydroanthracene were dissolved in 40 ml of tetrahydrofuran and 8.7 ml of methanolic hydrochloric acid. 1.3 Parts of a 10% palladium-on-carbon catalyst were added and the mixture was hydrogenated with 896 ml gaseous hydrogen at 30°-35° C. and normal pressure within 30 minutes. The catalyst was filtered off, and the filtrate concentrated. 4 Parts of 9-amino-1,2,3,4,4a,9,9a,10-octahydroanthracene hydrochloride, mp. 240°-245° C., were obtained. The hydrochloride was dissolved in water, and sodium hydroxide was added to adjust the pH-value to pH 8. The alkaline solution was extracted with ether. The combined etheral phases were dried with Na2SO4, filtered and concentrated. 2.8 Parts (70% of theory) of 9-amino-1,2,3,4,4a,9,9a,10-octahydroanthracene (int. 13), mp. 37°-39° C., were obtained. The amine-product consists of a mixture of at least 3 stereochemical isomers.

Workup

  1. extractionThe alkaline solution was extracted with ether
  2. dry with materialThe combined etheral phases were dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e9406a7536364b9c90142a9a4c8eff78
Source dataset
uspto-grants-1989_05
Patent number
US04830664

Reaction notes

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