Ammonium Chloride → 6-Amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

HRID 519206Notes

Reaction equation

HRID 519206 reaction equation
[CH3:1][CH:2]1[N:15]2[C:6]([CH2:7][O:8][C:9]3[C:14]2=[CH:13][C:12]([N+:16]([O-])=O)=[CH:11][CH:10]=3)=[N:5][NH:4][C:3]1=[O:19].[Cl-].[NH4+]>CO.[Zn]>[NH2:16][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][C:6]1[N:15]2[CH:2]([CH3:1])[C:3](=[O:19])[NH:4][N:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86727620HCID 86727620, compound

Product 1

HCID 867272916-Amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-oneYield 77%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-methyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (10 g, 38.2 mmol) and ammonium chloride (20.5 g, 382.0 mmol) in MeOH (200 mL) was added zinc powder (24.8 g, 382.0 mol) and the resulting mixture was stirred for 24 h at 25° C. The reaction mixture was filtered and the filtrate was washed with methanol (5×30 mL). The filtrate was combined and concentrated in vacuo and the residue was purified by chromatography on silica gel (eluting with 10% MeOH in DCM) to give 6-amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (6.8 g, 77%) as a yellow solid. 1H NMR (DMSO-d6, 400 MHz): δ 10.72 (s, 1H), 6.67 (d, J=8.4 Hz, 1H), 6.42 (d, J=2.4 Hz, 1H), 6.15 (q, J=8.4 Hz, J=2.4 Hz, 1H), 4.82 (brs, 2H), 4.52 (q, J=6.4 Hz, 1H), 4.43 (d, J=12.8 Hz, 2H), 1.30 (d, =6.4 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with methanol (5×30 mL)
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by chromatography on silica gel (eluting with 10% MeOH in DCM)

Sources & evidence

ORD record
ord-1457538487044c2b895bf9f8594cbef6
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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