Hydrochloric Acid → 2-(2H-benzo[d][1,2,3]triazol-2-yl)-6-(hydroxymethyl)-4-methoxyphenol

HRID 1691506

Reaction equation

[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([N:11]=[N:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)[C:4]=1[OH:22].[OH-].[Na+].C(S(O)=O)(N)=N.Cl>O.C(O)C>[N:12]1[N:11]([C:5]2[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([CH2:2][OH:1])[C:4]=2[OH:22])[N:19]=[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=12

Participants

Conditions

Temperature: 80 °C

Procedure

In a 500 ml round bottom flask equipped with a magnetic stirrer, regular addition funnel, powder addition funnel, and nitrogen inlet was added 23.6 g (77.7 mmol) 2-(hydroxymethyl)-4-methoxy-6-((2-nitrophenyl)diazenyl)phenol and 200 ml ethanol. NaOH (18.8 g, 470 mmol) was dissolved in 100 ml deionized water and approximately one-fourth was added dropwise to the reaction mixture. The mixture was heated to 80° C. and 25.1 g (232 mmol) formamidine sulfinic acid and the remaining sodium hydroxide solution were concurrently added dropwise to the reaction mixture over 30 minutes. The mixture was stirred at 80° C. for 3 hours, poured into 3.5 L water, and then acidified to pH 4 using 1 N HCl. The resultant solid was collected by filtration and worked up as in Example 5 to give a light yellow solid (4.3 g, 20.5%).

Workup

customIn a 500 ml round bottom flask equipped with a magnetic stirrer, regular addition funnel, powder addition funnel, and nitrogen inlet
additionapproximately one-fourth was added dropwise to the reaction mixture
filtrationThe resultant solid was collected by filtration

Sources & evidence

ORD record: ord-5dc2f0cacd1c4705b250271c2a7a73a8
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153703B2

Linked notes

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