Dimethylformamide → HCID 12513755, compound

HRID 443742Notes

Reaction equation

HRID 443742 reaction equation
[C-]#N.[K+].C[N:5](C)C=O.[CH3:9][N:10]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13](=O)[O:12][C:11]1=O>O>[NH:5]=[C:9]1[C:13](=[O:12])[C:14]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:10]1[CH3:11]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 9032Potassium CyanideHCID 25160N-Methylisatoic anhydride

Product 1

HCID 12513755HCID 12513755, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 1.3 g. (0.021 moles) of pulverized potassium cyanide in 75 ml. of dimethylformamide (distilled over calcium hydride) at 100° C. is added dropwise, over a period of 15 minutes, a solution containing 3.6 g (0.02 moles) of 1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione in 35 ml. of dimethylformamide (distilled over calcium hydride), after which time the reaction mixture is stirred at 100° C. for an additional 5 minutes. The resultant mixture is then poured into cold water and extracted into three 250 ml. portions of ether. After drying the organic phase over sodium sulfate, the excess solvent is removed and the resultant precipitate is filtered, washed with ether and dried in vacuo to yield 2-imino-1-methyl-3-indolinone, m.p.99°-120° C. (Yield: 49%).

Workup

  1. additionTo a suspension of 1.3 g
  2. extractionextracted into three 250 ml
  3. dry with materialAfter drying the organic phase over sodium sulfate
  4. customthe excess solvent is removed
  5. filtrationthe resultant precipitate is filtered
  6. washwashed with ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-11809d8e433f4dd48719887ea2a04bc8
Source dataset
uspto-grants-1981_04
Patent number
US04261894

Reaction notes

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