Hydrochloric Acid → HCID 17778350, compound

HRID 1954005Notes

Reaction equation

HRID 1954005 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3([N+:21]([O-])=O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]3[OH:20])[CH:5]=[CH:4][C:3]1=2.Cl>O.C(O)C.[Fe]>[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]3([NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]3[OH:20])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 17778352HCID 17778352, compound

Product 1

HCID 17778350HCID 17778350, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Compound 27 was suspended in water (2 ml) and ethanol (6 ml), and the suspension was added with concentrated hydrochloric acid (0.5 ml). The mixture was added with iron powder (220 mg) and then heated under reflux for 30 minutes. The reaction mixture was filtered to remove solid materials and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was then evaporated under reduced pressure to give o-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphtalenyl)-2-aminophenol (Compound 28, 80.5 mg, 85%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 minutes
  3. filtrationThe reaction mixture was filtered
  4. customto remove solid materials
  5. extractionthe filtrate was extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. customdried
  8. customthe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-f294e67c784a4b70ac96617eae42dfc4
Source dataset
uspto-grants-2000_09
Patent number
US06121256

Reaction notes

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