Hydrochloric Acid → HCID 67586054, compound

HRID 1938126Notes

Reaction equation

[C:1]([NH:6][C:7]1[CH:15]=[C:11]([C:12]([OH:14])=[O:13])[C:10]([OH:16])=[CH:9][CH:8]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].CC1C=C(C(C)(C)C)[C:21]([OH:28])=[C:20](C(C)(C)C)C=1.C(OC(=O)C)(=O)C.S(=O)(=O)(O)O.Cl>C(O)(=O)C>[C:21]([C:10]1([OH:16])[CH:9]=[CH:8][C:7]([NH:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[CH:15][CH:11]1[C:12]([OH:14])=[O:13])(=[O:28])[CH3:20]

Participants

Conditions

Temperature: 60 °C

Procedure

5-methacrylamidosalicylic acid (30 millimole, 6.7 g) was mixed with butylhydroxytoluene (20 mg), acetic anhydride (10.0 g), and acetic acid (15.0 g). After sealing the solution, its temperatures was raised to 60° C., and the solution was kept at 60° C. for 30 min while stirring. Then, a mixture (1.0 g) of concentrated sulfuric acid (1 part) with hydrochloric acid (10 parts) was added to the solution, followed by raising its temperature to 90° C., and kept at 90° C. for one hour to proceed the reaction. After the reaction was over, the solution was stood to cool to room temperature to give brown crystal. The crystal was filtrated, and recrystallized by a solution of 0.5% hydroquinone in methanol. Dried under a reduced pressure, 2-acetyl-5-methacrylamidosalicylic acid was obtained as pale reddish brown crystal having a needle shape: mp. 192.4° C., yield 2.54 g, 64.1%.

Workup

temperatureby raising its temperature to 90° C.
waitkept at 90° C. for one hour
customthe reaction
temperatureto cool to room temperature
customto give brown crystal
filtrationThe crystal was filtrated
customrecrystallized by a solution of 0.5% hydroquinone in methanol
customDried under a reduced pressure

Sources & evidence

ORD record: ord-551c1a2e5bf141be855c5bc119434fe1
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05693320

Reaction notes

Loading…