Acetic Acid → HCID 14402879, compound

HRID 1381825Notes

Reaction equation

HRID 1381825 reaction equation
C(O)(=O)C.O.[C:6]([CH2:8][N:9]1[C:14]2[CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=[CH:18][C:13]=2[O:12][CH2:11][C:10]1=[O:22])#[N:7]>[Fe].C(O)C>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[O:12][CH2:11][C:10](=[O:22])[N:9]([CH2:8][C:6]#[N:7])[C:14]=2[CH:15]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 14402878HCID 14402878, compound

Product 1

HCID 14402879HCID 14402879, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of ethanol (15 ml), acetic acid (1 g), water (25 ml) and iron (3 g) is stirred at 80° C., and 4-cyanomethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one (2.33 g) is added portionwise thereto. The whole is stirred at 80° C. until gas evolution ceases. The reaction mixture is mixed with active carbon (1 g) and ethanol (20 ml), refluxed for 15 minutes, and filtered. The filtrate is poured into chilled water. The deposited crystals are collected by filtration, and dried to obtain 6-amino-4-cyanomethyl-2H-1,4-benzoxazin-3(4H)-one (1.51 g).

Workup

  1. stirringThe whole is stirred at 80° C. until gas evolution ceases
  2. temperaturerefluxed for 15 minutes
  3. filtrationfiltered
  4. additionThe filtrate is poured
  5. temperatureinto chilled water
  6. filtrationThe deposited crystals are collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-715ca77a502248729df48cda7b5786db
Source dataset
uspto-grants-1989_02
Patent number
US04804394

Reaction notes

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