Benz(c)acridine-7-carboxylic acid → HCID 18006808, compound

HRID 2288576Notes

Reaction equation

HRID 2288576 reaction equation
[CH:1]1[C:18]2[C:17]3[C:8](=[C:9]([C:19]([OH:21])=[O:20])[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[N:16]=3)[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1>S(Cl)(Cl)=O>[CH:1]1[C:18]2[C:17]3[C:8](=[C:9]([C:19]([O:21][C:1]4[CH:18]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[O:20])[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[N:16]=3)[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 147573Benz(c)acridine-7-carboxylic acid

Product 1

HCID 18006808HCID 18006808, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

Benz[c]acridine-7-carboxylic acid (6.0 g) was suspended in 75 mL thionyl chloride (3-10 mL) and reaction mixture was refluxed for 4 h. The solvent was removed under reduced pressure and the product dissolved in 75 mL of CH2Cl2. Pyridine (8.9 mL) and phenol (2.27 g) were added and the solution was stirred for 3 days at room temperature under Ar. Purification was effected by chromatography on silica gel (50% CH2Cl2 /hexane) to yield 3.05 g of the pure product as a light brown solid. 1H NMR (CDCl3) δ 7.40 (t, 1H), 7.48-7.59 (m, 4H), 7.71-8.01 (m, 7H), 8.259 (d, 1H, J=7.8 Hz), 8.465 (d, 1H, J=7.8 Hz), 9.54-9.57 (m, 1H).

Workup

  1. customreaction mixture
  2. temperaturewas refluxed for 4 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe product dissolved in 75 mL of CH2Cl2
  5. additionPyridine (8.9 mL) and phenol (2.27 g) were added
  6. customPurification

Sources & evidence

ORD record
ord-0887096e62d34dee9b888a3a42772d96
Source dataset
uspto-grants-2000_07
Patent number
US06090571

Reaction notes

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