Acetic Acid → HCID 12773908, compound

HRID 1284062Notes

Reaction equation

C(O)(=O)C.C(O[CH:8](OCC)[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:13][CH:12]=1)C.[ClH:24].[OH:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:34]=1[OH:35])[CH2:29][CH2:30][NH2:31]>Cl.O>[ClH:24].[S:17]([C:14]1[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH:8]2[C:32]3[C:28](=[CH:27][C:26]([OH:25])=[C:34]([OH:35])[CH:33]=3)[CH2:29][CH2:30][NH:31]2)=[CH:16][CH:15]=1)(=[O:19])(=[O:20])[NH2:18]

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of acetic acid (23 ml), water (6.6 ml) and concentrated hydrochloric acid (15 drops) was added (4-sulfamoylphenoxy)acetaldehyde diethyl acetal (2.3 g), and the mixture was heated for 20 minutes at 110°C. To the solution was added 3,4-dihydroxyphenethylamine hydrochloride (1.2 g), and the mixture was heated for 3.5 hours at the same temperature. After the reaction, the reaction mixture was concentrated to dryness under reduced pressure. The residue was crystallized by adding acetone, and the crystals were recrystallized from a mixed solvent of methanol and acetone to give 1-(4-sulfamoylphenoxy)methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.8 g), mp 270°C (dec.).

Workup

temperaturethe mixture was heated for 3.5 hours at the same temperature
customAfter the reaction
concentrationthe reaction mixture was concentrated to dryness under reduced pressure
customThe residue was crystallized
additionby adding acetone
customthe crystals were recrystallized from a mixed solvent of methanol and acetone

Sources & evidence

ORD record: ord-7a1547f496744b4daeec31e7c4a6266e
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03978063

Reaction notes

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