Water → 103361-38-2

HRID 235579Notes

Reaction equation

HRID 235579 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[N:9]([CH2:13][C:14]#[CH:15])[C:8]=2[CH:16]=1)([O-])=O.O>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[N:9]([CH2:13][C:14]#[CH:15])[C:8]=2[CH:16]=1

Participants

6

Reactant 2

HCID 962WaterHCID 14457357HCID 14457357, compound

Product 1

HCID 13653298103361-38-2Yield 54.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Electrolytic iron (11.39 g) was suspended in 5% aqueous acetic acid solution (22 ml) and heated to 80° C. To the suspension, a solution of 5-nitro-3-(2-propynyl)-3H-benzoxazol-2-one (4.15 g) in acetic acid (20 ml) and ethyl acetate (20 ml) was dropwise added, and the resultant mixture was stirred at 70° C. for 3 hours. After being allowed to cool, water was added to the mixture, which was then extracted with ethyl acetate. The extract was washed with water and sodium bicarbonate solution, dried and concentrated to give 5-amino-3-(2-propynyl)-3H-benzoxazol-2-one (1.95 g). m.p., 102.1° C.

Workup

  1. temperatureto cool
  2. extractionwas then extracted with ethyl acetate
  3. washThe extract was washed with water and sodium bicarbonate solution
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5f1c88ec02fd4d37ae6987156f6643cf
Source dataset
uspto-grants-1987_02
Patent number
US04640707

Reaction notes

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