Acetic Anhydride → 3-(9-Ethyl-8-oxo-8,9-dihydro-3H-3,4,9-triaza-cyclopenta[a]naphthalen-7-yl)-5-methoxy-benzoic acid

HRID 2261189Notes

Reaction equation

HRID 2261189 reaction equation
C(OC(=O)C)(=[O:3])C.C([O:10][C:11](=[O:36])[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([C:20]2[C:29](=N)[N:28]([CH2:31][CH3:32])[C:27]3[C:22](=[CH:23][N:24]=[C:25]4[NH:35][CH:34]=[CH:33][C:26]4=3)[CH:21]=2)[CH:13]=1)C>>[CH2:31]([N:28]1[C:27]2[C:22](=[CH:23][N:24]=[C:25]3[NH:35][CH:34]=[CH:33][C:26]3=2)[CH:21]=[C:20]([C:14]2[CH:13]=[C:12]([CH:17]=[C:16]([O:18][CH3:19])[CH:15]=2)[C:11]([OH:10])=[O:36])[C:29]1=[O:3])[CH3:32]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 178469309HCID 178469309, compound

Product 1

HCID 248968743-(9-Ethyl-8-oxo-8,9-dihydro-3H-3,4,9-triaza-cyclopenta[a]naphthalen-7-yl)-5-methoxy-benzoic acid

Conditions

Temperature
120 °C

Procedure

Acetic anhydride (0.123 mL, 1.3 mmol) is added to (3-(9-ethyl-8-imino-8,9-dihydro-3H-3,4,9-triaza-cyclopenta[a]naphthalen-7-yl)-5-methoxy-benzoic acid ethyl ester (100 mg, 0.26 mmol) in sealed tube and heated at 120° C. for 2.5 hr. The acetic anhydride is evaporated and 6N HCl (3 mL) is added and the mixture is again heated at 105° C. for 1 hr. The reaction mixture is brought to room temperature and poured in ice cold water. The acid is crystallized out and filtered. It is washed with water and dried to give the desired product. MS m/z 364.2 (M+1).

Workup

  1. customThe acetic anhydride is evaporated
  2. addition6N HCl (3 mL) is added
  3. temperaturethe mixture is again heated at 105° C. for 1 hr
  4. customis brought to room temperature
  5. additionpoured in ice cold water
  6. customThe acid is crystallized out
  7. filtrationfiltered
  8. washIt is washed with water
  9. customdried

Sources & evidence

ORD record
ord-9f53dd61e086490791c05b555fe0ca02
Source dataset
uspto-grants-2010_12
Patent number
US07846923B2

Reaction notes

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