9-Amino-12-hydroxy-9,10-dihydro-9,10-ethanoanthracene → 9,10-Dihydro-9,10-methanoanthracene-9-carboxaldehyde

HRID 27949Notes

Reaction equation

HRID 27949 reaction equation
N[C:2]12[CH:17]([OH:18])[CH2:16][CH:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=31)[C:8]1[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=1.N([O-])=O.[Na+]>Cl.O>[CH:17]([C:2]12[CH2:16][CH:9]([C:8]3[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=31)[C:10]1[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:18]

Participants

5

Reactant 2

HCID 124041369-Amino-12-hydroxy-9,10-dihydro-9,10-ethanoanthraceneHCID 23668193Sodium Nitrite

Product 1

HCID 124041419,10-Dihydro-9,10-methanoanthracene-9-carboxaldehydeYield 75.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 9-amino-12-hydroxy-9,10-dihydro-9,10-ethanoanthracene (50 mg) in conc. hydrochloric acid (2 ml) and water (2 ml) was added a solution of sodium nitrite (112 mg) in water (1.0 ml) at 0° C. The resulting mixture was stirred at 0° C. for 1 hour and at room temperature for 5 hours. The reaction mixture was diluted with water and extracted with benzene. The benzene layer was washed with water, dried over sodium sulfate and evaporated to dryness to give crude crystals of 9-formyl-9,10-dihydro-9,10-methanoanthracene (35 mg).

Workup

  1. extractionextracted with benzene
  2. washThe benzene layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-d9eccbb1cef34c37ab2683206d182317
Source dataset
uspto-grants-1980_09
Patent number
US04224344

Reaction notes

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