4-Nitroaniline → HCID 15044295, compound

HRID 1748925Notes

Reaction equation

HRID 1748925 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:11]([O-])=O.[Na+].[CH2:15]([O:17][C:18]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][C:19]=1[NH2:20])[CH3:16]>O.Cl>[CH2:26]([O:25][C:22]1[CH:21]=[C:19]([N:20]=[N:8][C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:18]([O:17][CH2:15][CH3:16])=[CH:24][C:23]=1[NH2:11])[CH3:27]

Participants

6

Reactant 3

HCID 74754-NitroanilineHCID 66756Benzenamine, 2,5-diethoxy-HCID 23668193Sodium Nitrite

Product 1

HCID 15044295HCID 15044295, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Procedure

4-Nitroaniline (6.9 g, 0.05 mol) is suspended in water (150 ml) and 35% HCl (17.3 g) is added. To this is added a solution of sodium nitrite (3.6 g, 0.053 mol) at 0-5° C., pH<1. Once all solid has dissolved, excess nitrous acid is destroyed by addition of sulfamic acid and the solution is then added dropwise to a solution of 2,5-diethoxyaniline (9.4 g, 0.052 mol) in water (300 ml) and 35% HCl

Workup

  1. dissolutionOnce all solid has dissolved
  2. customexcess nitrous acid is destroyed by addition of sulfamic acid

Sources & evidence

ORD record
ord-ee7c702598074ea393ea0716819e3da7
Source dataset
uspto-grants-2015_10
Patent number
US09152006B2

Reaction notes

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