Phloroglucinol → 5-Chloro-1,3-dihydroxy-10H-acridin-9-one

HRID 1772560Notes

Reaction equation

HRID 1772560 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[OH:12][C:13]1[CH:18]=[C:17](O)[CH:16]=[C:15]([OH:20])[CH:14]=1>CC(C)=O>[Cl:11][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:2]=1[NH:1][C:17]1[CH:16]=[C:15]([OH:20])[CH:14]=[C:13]([OH:12])[C:18]=1[C:4]2=[O:6]

Participants

4

Reactant 2

HCID 359PhloroglucinolHCID 808072-Amino-3-chlorobenzoic acid

Product 1

HCID 54829325-Chloro-1,3-dihydroxy-10H-acridin-9-oneYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
230 °C

Procedure

A 250-mL sealed reactor was charged with 2-amino-3-chlorobenzoic acid (8.58 g, 50 mmol, and 1,3,5-trihydroxybenzene (110 mg, 1.0 mmol). The mixture was then heated to 230° C. for 40 min. The solids melted after ˜10 minutes and stayed as liquid for ˜1 minute before solidifying again. The mixture was cooled to room temperature and acetone (600 mL) was used to break the solids and transferred to a 1-L Erlenmeyer flask. The slurry was stirred for 30 minutes with periodic breaking of the solid with a spatula2. The solid was filtered and washed with acetone (200 mL), affording a dark yellow to brown powder. The powder was then triturated in hot methanol (1.5 L) at 60° C. for 30 minutes and filtered after the slurry cooled to ˜30° C. and washed with methanol (200 mL) to afford the product 3 (4.87 g, 37%) as yellow solid. 1H NMR (DMSO-d6): 6.06 (1H, d, J=2.3), 6.81 (1H, d, J=2.0), 7.23 (1H, t, J=8.1), 7.87 (1H, d, J=7.3), 8.11 (1H, d, J=7.3), 10.64 (1H, s), 10.97 (1H, s): LC-MS: m/z+1=262.1.

Workup

  1. customA 250-mL sealed reactor
  2. waitstayed as liquid for ˜1 minute
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationThe solid was filtered
  5. washwashed with acetone (200 mL)
  6. customaffording a dark yellow to brown powder
  7. customThe powder was then triturated in hot methanol (1.5 L) at 60° C. for 30 minutes
  8. filtrationfiltered after the slurry
  9. temperaturecooled to ˜30° C.
  10. washwashed with methanol (200 mL)

Sources & evidence

ORD record
ord-30fb35eb21124546ab7616dc08debbe1
Source dataset
uspto-grants-2016_02
Patent number
US09249249B2

Reaction notes

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