2,4,4-Trimethyl-5-[(5-nitro-2-pyridyl)oxy]-3,1-benzoxazine → 6-[(2,4,4-Trimethyl-3,1-benzoxazin-5-yl)oxy]pyridin-3-amine

HRID 527662Notes

Reaction equation

HRID 527662 reaction equation
[CH3:1][C:2]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]2[C:10]([O:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][N:16]=3)=[CH:11][CH:12]=[CH:13][C:4]=2[N:3]=1>CCO>[CH3:1][C:2]1[O:7][C:6]([CH3:8])([CH3:9])[C:5]2[C:10]([O:14][C:15]3[N:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=3)=[CH:11][CH:12]=[CH:13][C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 679601632,4,4-Trimethyl-5-[(5-nitro-2-pyridyl)oxy]-3,1-benzoxazine2×

Product 1

HCID 679602016-[(2,4,4-Trimethyl-3,1-benzoxazin-5-yl)oxy]pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4,4-trimethyl-5-[(5-nitro-2-pyridyl)oxy]-3,1-benzoxazine (Intermediate 203, 220 mg, 0.70 mmol) in EtOH (3 mL) palladium on carbon 10% w/w (25 mg) was added and the resulting mixture was stirred for 40 minutes under hydrogen atmosphere (2 bar) at room temperature. The catalyst was filtered off and washed with EtOH (3×10 mL). The filtrate was concentrated to the title compound (185 mg) as greenish solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with EtOH (3×10 mL)
  3. concentrationThe filtrate was concentrated to the title compound (185 mg) as greenish solid

Sources & evidence

ORD record
ord-57b91b1e84f04300993933c7062cbab5
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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