HCID 22349277, compound → HCID 89553772, compound

HRID 590388Notes

Reaction equation

HRID 590388 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, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

100 mg (0.52 mmol) of 3-amino-4-[(3-hydroxypropyl)amino]benzonitrile (Intermediate 12) are suspended in 0.5 ml of 5N aqueous HCl. After cooling externally with an ice/water bath, a solution of 54.12 mg (0.78 mmol) of sodium nitrite in 0.4 ml water is added dropwise with stirring. After 3.5 hr excess water is added and the solid is extracted with dichloromethane, washed with water, dried and concentrated to give 104 mg of pure title compound (96% yield).

Workup

  1. temperatureAfter cooling externally with an ice/water bath
  2. extractionthe solid is extracted with dichloromethane
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-168104b172ff48099d9f31bf5ea463ed
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

Loading…