Methyl 3-methoxy-4-(6-nitro-2,3-di-hydrobenz-1,4-oxazin-4-ylmethyl)benzoate → Methyl 4-(6-amino-2,3-dihydrobenz-1,4-oxazin4-ylmethyl)-3-methoxybenzoate

HRID 1646343Notes

Reaction equation

HRID 1646343 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[C:19]2[CH:20]=[C:21]([N+:24]([O-])=O)[CH:22]=[CH:23][C:18]=2[O:17][CH2:16][CH2:15]1)[C:6]([O:8][CH3:9])=[O:7].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]2[O:17][CH2:16][CH2:15][N:14]([CH2:13][C:12]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=3[O:2][CH3:1])[C:19]=2[CH:20]=1

Participants

5

Reactant 2

HCID 14763125Methyl 3-methoxy-4-(6-nitro-2,3-di-hydrobenz-1,4-oxazin-4-ylmethyl)benzoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 14763126Methyl 4-(6-amino-2,3-dihydrobenz-1,4-oxazin4-ylmethyl)-3-methoxybenzoateYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium-on-carbon (10% w/w, 0.2 g.) was added to a solution of (G) (0.69 g.) in ethyl acetate (50 ml.) in a hydrogenation bottle and the mixture hydrogenated at a pressure of 3.17 bars of hydrogen. When the uptake of hydrogen had ceased, catalyst was removed by filtration through diatomaceous earth. The filter pad was washed with ethyl acetate and the filtrate and washings were evaporated to give methyl 4-(6-amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)-3-methoxybenzoate (0.625 g., 91%) as a foam; NMR: 3.1 (br s,2 H, NH2), 3.3 (t,2 H, OCH2CH2N), 3.85 (m,6 H, OCH3 +CO2CH3), 4.2 (t,2 H, OCH2CH2N), 4.45 (s, 2 H, CH2 --Ar), 6.0 (m,2 H), 6.55 (d,1 H), 7.3 (d,1 H), 7.55 (m, 2 H).

Workup

  1. customcatalyst was removed by filtration through diatomaceous earth
  2. washThe filter pad was washed with ethyl acetate
  3. customthe filtrate and washings were evaporated

Sources & evidence

ORD record
ord-87e3d44435494be4bd4eee94ddc41f54
Source dataset
uspto-grants-1993_01
Patent number
US05179112

Reaction notes

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