Ammonia → 3-[(2-Dimethylamino-4-nitro-benzoyl)-amino]-2-amino-6-methoxy-pyridine

HRID 3851Notes

Reaction equation

HRID 3851 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.Cl.Cl.[NH2:18][C:19]1[C:24]([NH2:25])=[CH:23][CH:22]=[C:21]([O:26][CH3:27])[N:20]=1.O.N>P(Cl)(Cl)(Cl)=O>[CH3:15][N:2]([CH3:1])[C:3]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5]([NH:25][C:24]1[C:19]([NH2:18])=[N:20][C:21]([O:26][CH3:27])=[CH:22][CH:23]=1)=[O:7]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 30239196-Methoxy-2,3-pyridinediamine HClHCID 201382202-(Dimethylamino)-4-nitrobenzoic acid

Product 1

HCID 135324023-[(2-Dimethylamino-4-nitro-benzoyl)-amino]-2-amino-6-methoxy-pyridine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

An amount of 1.05 gm of 2-dimethylamino-4-nitro-benzoic acid is suspended in 35 ml of phosphorus oxychloride, and 1.05 gm of 2,3-diamino-6-methoxy-pyridine dihydrochloride are added thereto. The mixture is refluxed for 5 minutes, left to cool for 15 minutes with stirring, and finally decomposed with water. The solution obtained is cooled and poured onto a mixture of ice and concentrated ammonia. The product is then precipitated. It is subjected to suction filtration, washed with water, and dried in a circulating air drier at 50° C.

Workup

  1. temperatureThe mixture is refluxed for 5 minutes
  2. waitleft
  3. temperatureto cool for 15 minutes
  4. customThe solution obtained
  5. temperatureis cooled
  6. customThe product is then precipitated
  7. filtrationIt is subjected to suction filtration
  8. washwashed with water
  9. customdried in a circulating air drier at 50° C.

Sources & evidence

ORD record
ord-ed32d25e0c7c45dfb2b09ee2c01e0cd2
Source dataset
uspto-grants-1988_02
Patent number
US04722929

Reaction notes

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