Hydrochloric Acid → HCID 23050707, compound

HRID 1650997Notes

Reaction equation

HRID 1650997 reaction equation
[N:1](=[C: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)O.[H][H].[ClH:19]>O1CCCC1.[Pd]>[ClH:19].[NH2:1][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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73165165HCID 73165165, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23050707HCID 23050707, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

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. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-743cd08580ee4825ac30e35a4a240e55
Source dataset
uspto-grants-1990_05
Patent number
US04927449

Reaction notes

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