Cyclohexane → HCID 13827094, compound

HRID 1252729Notes

Reaction equation

HRID 1252729 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]2[C:8](=[O:15])[O:9][C:10]([O:12][CH2:13][CH3:14])=[N:11][C:6]=2[CH:5]=1)([O-])=O.C1CCCCC1>C1C=CC=CC=1.[Pd]>[NH2:1][C:4]1[CH:17]=[CH:16][C:7]2[C:8](=[O:15])[O:9][C:10]([O:12][CH2:13][CH3:14])=[N:11][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 8078CyclohexaneHCID 13827089HCID 13827089, compound

Product 1

HCID 13827094HCID 13827094, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

7-Nitro-2-ethoxy-4H-3,1-benzoxazin-4-one (1 gm, 4.2 m mol.), 10% Pd-C (1 gm), and cyclohexane (2.5 ml) were refluxed in dry benzene (50 ml) under anhydrous conditions for 3 hours. The hot reaction mixture was filtered immediately through celite and the catalyst on celite was washed with hot benzene (25 ml). The combined filtrate was evaporated to dryness under reduced pressure. The residue was stirred in anhydrous ether (30 ml) to give 410 mg (47%) of the title compound, 7-amino-2-ethoxy-4H-3,1-benzoxazin-4-one, as a pale yellow powder, after filtration. The product can be further purified by chromatography on silica gel column, if necessary (silica gel 60; EtOAc:pet. ether=1:2); m. p. 185°-187° C.; IR (KBr): νmax 3425, 3330 cm-1 (NH2), 1740 cm-1 (C=O), 1640 cm-1 (C=N); H'NMR (CDCl3): δ1.43 ppm (t, J=7.1 Hz, 3H, OCH2CH3), 4.30 ppm (b, 2H, NH2), 4.75 ppm (q, J=7.1 Hz, 2H, OCH2CH3), 6.5-7.98 ppm (m, 3H, aromatic protons).

Workup

  1. filtrationThe hot reaction mixture was filtered immediately through celite
  2. washthe catalyst on celite was washed with hot benzene (25 ml)
  3. customThe combined filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b75ce80845174af8b6c18f89ac4773ac
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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