HCID 22349277, compound → HCID 89553772, compound

HRID 590408Notes

Reaction equation

HRID 590408 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH2:12][CH2:13][OH:14])[C:5]#[N:6].[N:15]([O-])=O.[Na+]>Cl.O>[OH:14][CH2:13][CH2:12][CH2:11][N:10]1[C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[N:1]=[N:15]1

Participants

5

Reactant 2

HCID 22349277HCID 22349277, compound2×HCID 23668193Sodium Nitrite

Product 1

HCID 89553772HCID 89553772, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a vigorously stirred solution of 3-amino-4-[(3-hydroxypropyl)amino]benzonitrile (Intermediate 96, 11.5 g, 0.06 mol) in aqueous HCl (105 mL of a 5N HCl solution) was added, dropwise an 0° C., a solution of sodium nitrite (6.2 g, 0.09 mol) in water (47 mL). After 3.5 hours of vigorously stirring at 0° C., water was added (200 mL) and the reaction mixture extracted with AcOEt (3×150 mL). The combined organic extracts were washed with water (3×100 mL) and brine, and the resulting organic phase was evaporated to dryness to deliver the title compound as a brownish solid (10.8 g, 86%) which was used without further purification.

Workup

  1. extractionthe reaction mixture extracted with AcOEt (3×150 mL)
  2. washThe combined organic extracts were washed with water (3×100 mL) and brine
  3. customthe resulting organic phase was evaporated to dryness
  4. customwas used without further purification

Sources & evidence

ORD record
ord-72066ed9e00e4890a6347ab1f70db228
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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