Sulfuric Acid → 4-[[4-[N,N-bis(hydroxylethyl)amino]phenyl]azo]pyridine

HRID 879090Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.[N+:8]([O-])([O-])=O.[Na+].S(=O)(=O)(O)O.[C:18]1([N:24]([CH2:28][CH2:29][OH:30])[CH2:25][CH2:26][OH:27])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[OH:27][CH2:26][CH2:25][N:24]([C:18]1[CH:23]=[CH:22][C:21]([N:8]=[N:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:20][CH:19]=1)[CH2:28][CH2:29][OH:30]

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 17274-Aminopyridine

HCID 8416N-Phenyl diethanolamine

HCID 24268Sodium Nitrate

Product 1

HCID 185519564-[[4-[N,N-bis(hydroxylethyl)amino]phenyl]azo]pyridine

Procedure

4-[[4-[N,N-Bis(hydroxylethyl)amino]phenyl]azo]pyridine (1) was prepared according to procedures described in Lin et al., J. Am. Chem. Soc., 118: 8034 (1996). Specifically, pyridin-4-amine was reacted with a mixture of sodium nitrate and sulfuric acid, followed by reaction with 2,2′-(phenylazanediyl)diethanol.

Sources & evidence

ORD record: ord-d2222b351be6466eabf7ee957693c45b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987710B2

Reaction notes

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