Carbon Dioxide → HCID 10470967, compound

HRID 2182183Notes

Reaction equation

HRID 2182183 reaction equation
[CH2:1]([N:8]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:27](=[O:29])=[O:28]>C1COCC1>[CH2:1]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]([C:27]([OH:29])=[O:28])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 10400992HCID 10400992, compoundHCID 178418339Butyllithium

Product 1

HCID 10470967HCID 10470967, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of Compound 5, N-benzylacridan (10 g, 37 mmol) in 200 mL of dry THF under inert atmosphere was cooled to 78° C. and 25.0 mL of 2.5 M n-butyllithium in hexanes (37.5 mmol) was added dropwise over 15 min. The solution was stirred at −78° C. for 1 h and then warmed to room temperature over 45 min. The reaction mixture was again cooled to −78° C. and ca. 200 g of crushed dry ice was added causing a precipitate to form. The reaction was allowed to slowly warm to room temperature and stirring under argon was continued over night. The mixture was evaporated, the solid was then suspended in 300 mL of water and acidified to pH 3 with 12N HCl. The solid was collected, washed with water, dissolved in CH2Cl2, dried over sodium sulfate and concentrated to afford 11 g of N-benzyl-acridan-9-carboxylic acid. 1H NMR: (CDCl3) ∂ 4.99 (s, 1H), 5.12 (s, 2H), 6.72-6.75 (d, 2H), 6.88-6.94 (t, 2H), 7.10-7.17 (m, 4H), 7.22-7.32 (m, 5H).

Workup

  1. temperaturewarmed to room temperature over 45 min
  2. temperatureThe reaction mixture was again cooled to −78° C.
  3. customto form
  4. temperatureto slowly warm to room temperature
  5. stirringstirring under argon
  6. waitwas continued over night
  7. customThe mixture was evaporated
  8. customThe solid was collected
  9. washwashed with water
  10. dissolutiondissolved in CH2Cl2
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-909080adc3f543f0b87c026c736293c8
Source dataset
uspto-grants-2005_05
Patent number
US06897036B2

Reaction notes

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