HCID 13649003, compound → HCID 13649004, compound

HRID 235580Notes

Reaction equation

HRID 235580 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]#[CH:11])[C:5]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:4]=2[O:3]1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:16][C:13]1[CH:14]=[CH:15][C:4]2[O:3][CH:2]([CH3:1])[C:7](=[O:8])[N:6]([CH2:9][C:10]#[CH:11])[C:5]=2[CH:12]=1

Participants

5

Reactant 1

HCID 13649003HCID 13649003, compound

Product 1

HCID 13649004HCID 13649004, compoundYield 50.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methyl-6-nitro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (5 g) in acetic acid (50 ml) and ethyl acetate (50 ml) was dropwise added to a mixture of iron powder (6 g) and 5% aqueous acetic acid (50 ml), and the resultant mixture was heated under reflux for 1 hour. After being allowed to cool, iron powder was removed by filtration and the filtrate was admixed with water. The aqueous layer was extracted with ethyl acetate, and the extract was combined with the organic layer, washed with a saturated sodium bicarbonate solution, dried and concentrated. The residue was crystallized from methanol to give 6-amino-2-methyl-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (2.2 g). m.p., 158°-159° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureto cool
  3. customiron powder was removed by filtration
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with a saturated sodium bicarbonate solution
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-12430f33cff541048b119aec84a9e5ed
Source dataset
uspto-grants-1987_02
Patent number
US04640707

Reaction notes

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