HCID 21480678, compound → HCID 21480627, compound

HRID 1721779Notes

Reaction equation

HRID 1721779 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][C:5]([C:20]([O:22][CH3:23])=[O:21])([C:6]4[C:11]3=[CH:10][CH:9]=[C:8]([N+:17]([O-])=O)[CH:7]=4)[C:4]=2[CH:3]=1>C(O)C>[NH2:17][C:8]1[CH:9]=[CH:10][C:11]2[CH:12]3[CH2:16][C:5]([C:20]([O:22][CH3:23])=[O:21])([C:4]4[C:13]3=[CH:14][CH:15]=[C:2]([Cl:1])[CH:3]=4)[C:6]=2[CH:7]=1

Participants

3

Reactant 1

HCID 21480678HCID 21480678, compound

Product 1

HCID 21480627HCID 21480627, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of methyl 2-chloro-7-nitro-9,10-dihydro-9,10-methano-9-anthracenecarboxylate (described in example 35b) (7.36 g, 22.32 mmol) in ethanol (150 mL) was added stannous chloride dihydrate (25.2 g, 112 mmol, 5 eq). The reaction was heated to reflux at which time it became homogeneous. After heating for 2.5 h, the solution was cooled to 0° C. and quenched with ice followed by 10% NaOH (200 mL). The aqueous phase was extracted with ethyl acetate (3×150 mL). Combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and reduced to a solid. The reaction product was purified by flash chromatography over silica gel (400 mL, eluent: 25% ethyl acetate in hexane) to yield 5.06 g (76%) of the title compound. TLC analysis (Rf 0.16, 30% ethyl acetate in hexane). MS (CI, CH4) m/z 300 (M+1,100), 302 (33), 328 (M+29,9), 264 (12), 182 (11), 121 (11), 89 (44).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux at which time it
  3. temperatureAfter heating for 2.5 h
  4. customquenched with ice
  5. extractionThe aqueous phase was extracted with ethyl acetate (3×150 mL)
  6. dry with materialCombined organic extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe reaction product was purified by flash chromatography over silica gel (400 mL, eluent: 25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-55594486b2834f669f023d51cf8b2647
Source dataset
uspto-grants-1996_04
Patent number
US05512575

Reaction notes

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