HCID 15107813, compound → HCID 14884397, compound

HRID 846096Notes

Reaction equation

HRID 846096 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:15]2[CH2:16][CH2:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][NH:11][C:12]([CH3:14])=[O:13].[N:22]([O-])=O.[Na+]>S(=O)(=O)(O)O.O>[NH:11]([CH2:10][CH2:9][N:8]1[C:7]2[CH:6]=[CH:5][C:4]([C:15]3[CH2:16][CH2:17][C:18](=[O:21])[NH:19][N:20]=3)=[CH:3][C:2]=2[N:1]=[N:22]1)[C:12]([CH3:14])=[O:13]

Participants

5

Reactant 2

HCID 15107813HCID 15107813, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14884397HCID 14884397, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

15.98 g (55.3 mmol) of 6-(3-amino-4-acetaminoethylamino-phenyl)-4,5-dihydro-3(2H)-pyridazinone are dissolved in 300 ml of 2N sulphuric acid, then cooled to 2°-5° C. and a solution of 4.2 g (61 mmol) of sodium nitrite in 70 ml of water is slowly added dropwise with stirring. After about one hour the cooling bath is removed and the mixture is stirred for a further hour at ambient temperature. The solids precipitated are suction filtered, stirred into 100 ml of a 5% sodium bicarbonate solution and suction filtered again after 10 minutes.

Workup

  1. temperaturecooled to 2°-5° C.
  2. customAfter about one hour the cooling bath is removed
  3. stirringthe mixture is stirred for a further hour at ambient temperature
  4. customThe solids precipitated
  5. stirringstirred into 100 ml of a 5% sodium bicarbonate solution and suction
  6. filtrationfiltered again after 10 minutes

Sources & evidence

ORD record
ord-67b35fcb954f4bdfaa093f633afdf5fc
Source dataset
uspto-grants-1992_08
Patent number
US05135932

Reaction notes

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