2-Nitropropane → HCID 18357635, compound

HRID 1763941Notes

Reaction equation

HRID 1763941 reaction equation
[N+](C(C)C)([O-])=[O:2].[Na].Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[O:18][N:17]=2)=[CH:12][CH:11]=1>C(O)C.CN(C)C=O>[CH:9]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[O:18][N:17]=2)=[CH:12][CH:11]=1)=[O:2]

Participants

6

Reactant 3

HCID 3982-NitropropaneHCID 5360545SodiumHCID 18357643HCID 18357643, compound

Product 1

HCID 18357635HCID 18357635, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

115.8 g of 2-nitropropane are introduced at about 30° C. into a solution of 23.13 g of sodium in 2,700 ml of anhydrous ethanol. The mixture is stirred for a further one hour and a solution of 288.1 g of 3-(p-bromomethyl-phenyl)-1,2-benzisoxazole in 350 ml of dimethylformamide is now added. Subsequently, the reaction mixture is warmed to 50° C., then stirred for 20 hours without external warming and finally cooled to -10° C. The product which has precipitated is filtered off with suction, washed with cold methanol and dried. This gives 107.4 g (48.1% of theory) of 3-(p-formylphenyl)-1,2-benzisoxazole in the form of a pale yellow powder with a melting point of 117° to 117.5° C. After recrystallising twice from ligroin, small, virtually colourless, glossy needles are obtained which melt at 117° to 117.5° C.

Workup

  1. stirringstirred for 20 hours
  2. temperaturewithout external warming
  3. temperaturefinally cooled to -10° C
  4. customThe product which has precipitated
  5. filtrationis filtered off with suction
  6. washwashed with cold methanol
  7. customdried
  8. customAfter recrystallising twice from ligroin
  9. customsmall, virtually colourless, glossy needles are obtained which melt at 117° to 117.5° C.

Sources & evidence

ORD record
ord-5946e25df71e4db6a0065dbbcd73a9da
Source dataset
uspto-grants-1978_09
Patent number
US04113938

Reaction notes

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