Acetic Acid → HCID 117988541, compound

HRID 63790Notes

Reaction equation

HRID 63790 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:11]3=[CH:20][C:21]([C:23]([O:25]C)=[O:24])=[CH:22][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)C>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[C:11]3=[CH:20][C:21]([C:23]([OH:25])=[O:24])=[CH:22][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 117987835HCID 117987835, compound

Product 1

HCID 117988541HCID 117988541, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 10a (14 mmol) was suspended in 150 mL of ethanol, and 30 mL of 2 M aqueous sodium hydroxide solution was added. The reaction mixture was refluxed to be a clear solution and the reaction was substantially completed. 2 mL of acetic acid was added. Most of the solvent was distilled off under reduced pressure, and the precipitates were filtered to give compound 11a (3.25 g, 68.5%). m.p.>300° C. 1H NMR (300 MHz, DMSO-d6): δ 7.91 (d, J=8.8 Hz, 2H), 7.71 (d, J=1.2 Hz, 1H), 6.99 (d, J=1.2 Hz, 1H), 6.59 (d, J=8.8 Hz, 2H), 5.49 (s, 2H), 4.02 (t, J=4.4 Hz, 4H), 3.77 (t, J=4.4 Hz, 4H). MS (EI) m/e (%): 339 (M+, 100).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. distillationMost of the solvent was distilled off under reduced pressure
  3. filtrationthe precipitates were filtered

Sources & evidence

ORD record
ord-3c322b9d73e843d19da04106e56b6603
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

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