Sodium Nitrite → HCID 178458288, compound

HRID 2288020Notes

Reaction equation

HRID 2288020 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[NH2:12])[N:8]=[C:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:20][CH2:21][CH3:22])[NH:6][C:5]2=[O:23].[N:24]([O-])=O.[Na+]>Cl.O>[CH2:20]([O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:7]1[NH:6][C:5](=[O:23])[C:4]2[CH:3]=[C:2]3[NH:1][N:24]=[N:12][C:11]3=[CH:10][C:9]=2[N:8]=1)[CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 135770535HCID 135770535, compound

Product 1

HCID 178458288HCID 178458288, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

6,7-diamino-2-(2-propoxyphenyl)-4(3H)-quinazolinone (0.15 g, 0.51 mmol) was suspended in 1N HCl (5 mL) and cooled in an ice-methanol bath. A solution of sodium nitrite (0.035 g) in water (1 mL) was added in one portion. The reaction was stirred in an ice bath for 30 minutes, then warmed to room temperature for 90 minutes. The precipitated solid was collected by filtration, washed with water, and dried to afford the title compound as a brown solid (0.42 mmol, 83%): mp dec>260° C.; LRMS [MH+] 308.

Workup

  1. temperaturecooled in an ice-methanol bath
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-316b7ae8fab941a785b06c93affc2f54
Source dataset
uspto-grants-2000_07
Patent number
US06087368

Reaction notes

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