HCID 19044647, compound → HCID 9990297, compound

HRID 1682504Notes

Reaction equation

HRID 1682504 reaction equation
[N+:1]([C:4]1[CH:17]=[C:16]2[C:7]([CH:8]=[C:9]3[C:14](=[CH:15]2)[CH2:13][CH2:12][CH2:11][CH2:10]3)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:17]=[C:16]2[C:7]([CH:8]=[C:9]3[C:14](=[CH:15]2)[CH2:13][CH2:12][CH2:11][CH2:10]3)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 19044647HCID 19044647, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9990297HCID 9990297, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4 mg (17.62 mmol) of 1,2,3,4-tetrahydro-7-nitroanthracene (John D. Scribner and James A. Miller; J. Chem. Soc., 5377 (1965)) and 0.5 g of palladium-on-carbon catalyst in 200 ml of methanol was shaken with hydrogen at 50 p.s.i. for 5 hours. The catalyst was removed by filtration and the filtrate was concentrated to give 3.4 g (97%) of 7-amino-1,2,3,4-tetrahydroanthracene. To a solution of 3.2 g (16.24 mmol) of the latter in 50 ml of dry tetrahydrofuran was added 2.7 g (26.7 mmol) of triethylamine followed by 3 g (24.9 mmol) of trimethylacetylchloride. After stirring at room temperature overnight, the solvent was removed and the residue was triturated with warm water to give 4.52 g (99%) of 7-trimethylacetylamino-1,2,3,4-tetrahydroanthracene, crystallized from methanol into colorless crystals of melting point 202°-204° C. and providing the following analysis:

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a06ff9035d13487f8832ecf8b2d97e3d
Source dataset
uspto-grants-1997_06
Patent number
US05635506

Reaction notes

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