Hydrochloric Acid → Perylenebutanoic acid

HRID 501893Notes

Reaction equation

HRID 501893 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]([C:8]1[C:25]2=[C:26]3[C:15]([C:16]4[C:27]5[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=5)[CH:19]=[CH:18][CH:17]=4)=[CH:14][CH:13]=[CH:12][C:11]3=[CH:10][CH:9]=1)=O.O.NN.[OH-].[K+].Cl>C(O)COCCO.O>[C:8]1([CH2:6][CH2:5][CH2:4][C:3]([OH:28])=[O:2])[C:25]2=[C:26]3[C:15]([C:16]4[C:27]5[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=5)[CH:19]=[CH:18][CH:17]=4)=[CH:14][CH:13]=[CH:12][C:11]3=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 866055493-Perylenoyl propanoic acid methyl ester

Product 1

HCID 86605548Perylenebutanoic acidYield 68.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
140 °C

Procedure

To a suspension of 3-perylenoyl propanoic acid methyl ester (360.2 mg, 0.983 mmol) in 2.0 mL diethylene glycol, 98% hydrazine hydrate (150.6 μL, 2.949 mmol) and powdered potassium hydroxide (275.3 mg, 4.916 mmol) were added. The reaction mixture was heated to 140° C. for 2 hrs, then to 190° C. and kept over night, cooled to room temperature, diluted with 20 mL water, acidified with 0.5 mL concentrated hydrochloric acid, the precipitate formed was filtered, washed with water to pH 7.0, dried on air or washed with acetone, then with a mixture chloroform-methanol (8:2 by vol.). The filtrate was concentrated in vacuo. The crude product was applied onto a silica gel column and eluted with chloroform to 20% methanol in chloroform to give perylenebutanoic acid (228.9 mg, 68.8%). Rf 0.66 (system 3). 1H-NMR (CDCl3/DMSO-d6, 20:1) (δ, ppm): 1.92 (quin., 2H, 3-CH2), 2.38 (t, 2H, J 7.00 Hz, 2-CH2), 3.03 (t, 2H, J 7.00 Hz, 4-CH2), 7.41 (d, 1H, J 7.82 Hz, Ar), 7.43-7.64 (m, 3H, Ar), 7.76 (d, 1H, J 3.42 Hz, Ar), 7.80 (d, 1H, J 3.41 Hz, Ar), 8.00 (d, 1H, J 8.49 Hz, Ar), 8.21-8.60 (m, 4H, Ar).

Workup

  1. additionwere added
  2. waitto 190° C. and kept over night
  3. temperaturecooled to room temperature
  4. customthe precipitate formed
  5. filtrationwas filtered
  6. washwashed with water to pH 7.0
  7. customdried on air
  8. washwashed with acetone
  9. concentrationThe filtrate was concentrated in vacuo
  10. washeluted with chloroform to 20% methanol in chloroform

Sources & evidence

ORD record
ord-3922d30300e54254bba3c4183093f7e6
Source dataset
uspto-grants-2010_08
Patent number
US07772402B2

Reaction notes

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