HCID 15283178, compound → HCID 15283179, compound

HRID 22187Notes

Reaction equation

HRID 22187 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:12]=[C:11]([O:13][CH2:14][CH3:15])[O:10][C:9](=[O:16])[C:8]=2[C:17]=1[CH2:18][CH3:19])([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[N:12]=[C:11]([O:13][CH2:14][CH3:15])[O:10][C:9](=[O:16])[C:8]=2[C:17]=1[CH2:18][CH3:19]

Participants

4

Reactant 1

HCID 15283178HCID 15283178, compound

Product 1

HCID 15283179HCID 15283179, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.75 g (2.8 mmoles) 6-nitro-5-ethyl-2-ethoxy-3,1-benzoxazin-4-one in 35 mL ethyl acetate was transferred to a Parr bottle. 0.40 g (0.38 mmoles) of 10% Pd/C catalyst was added. The sample was hydrogenated on a Parr shaker at ambient temperature and 1 atm pressure for 3 hours. The catalyst was removed by filtration through a pad of Celite. The filtrate was concentrated in vacuo to produce a bright yellow solid. There was obtained 0.58 g (86% yield) of 6-amino-5-ethyl-2-ethoxy-3,1-benzoxazin-4-one. NMR(CDCl3): 1.22 (t,3H,J=7.5 Hz), 1.42(t,3H,J=7.2 Hz), 3.14(q,2H,J=7.5 Hz), 4.44(q,2H,J=7.2 Hz), 7.09(d,1H,J=8.7 Hz), 7.14(d,1H,J=8.7 Hz). MS(m/z): 234(M+).

Workup

  1. customwas hydrogenated on a Parr shaker at ambient temperature
  2. customThe catalyst was removed by filtration through a pad of Celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto produce a bright yellow solid

Sources & evidence

ORD record
ord-8f12024f2c434531beb141a6d6a8a5aa
Source dataset
uspto-grants-1995_06
Patent number
US05428021

Reaction notes

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