Hydrazine hydrate (1:1) → 6-Bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

HRID 519200Notes

Reaction equation

HRID 519200 reaction equation
C([O:3][C:4](=O)[CH:5]([N:7]1[C:12]2[CH:13]=[C:14]([Br:17])[CH:15]=[CH:16][C:11]=2[O:10][CH2:9][C:8]1=S)[CH3:6])C.O.[NH2:21][NH2:22]>CCO>[Br:17][C:14]1[CH:13]=[C:12]2[C:11](=[CH:16][CH:15]=1)[O:10][CH2:9][C:8]1[N:7]2[CH:5]([CH3:6])[C:4](=[O:3])[NH:21][N:22]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 867276172-(6-Bromo-3-thioxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-propionic acid ethyl ester

Product 1

HCID 867273756-Bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-oneYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(6-bromo-3-thioxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-propionic acid ethyl ester (28 g, 81.4 mmol) in EtOH (100 mL) was added hydrazine hydrate (98%, 13.1 g, 162.8 mmol). The reaction mixture was stirred at ambient temperature overnight. The precipitate was collected by filtration and washed with cold EtOH (3×10 mL) to give 6-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one as a yellow solid (22.0 g, 74.3 mmol, 92%). 1H NMR (DMSO-d6, 400 MHz): δ 10.83 (s, 1H), 7.41 (d, J=2.0 Hz, 1H), 7.11 (d, J=2.0 Hz, J=8.4 Hz, 1H), 6.94 (d, J=8.4 Hz, 1H), 4.82 (q, J=6.8 Hz, 1H), 4.62 (d, J=13.2 Hz, 2H), 1.28 (d, J=6.8 Hz, 3H).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with cold EtOH (3×10 mL)

Sources & evidence

ORD record
ord-8152215f7df9430ba3684ab241be7c61
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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