Lithium Chloride → HCID 86727480, compound

HRID 519104Notes

Reaction equation

HRID 519104 reaction equation
C[O:2][C:3]1[CH:16]=[C:15]2[C:6]([N:7]3[C:12]([CH2:13][O:14]2)=[N:11][NH:10][C:9](=[O:17])[CH:8]3[CH3:18])=[CH:5][C:4]=1[N+:19]([O-:21])=[O:20].NC1C=CC(OC)=CC=1O.[Cl-].[Li+]>CN(C=O)C>[OH:2][C:3]1[CH:16]=[C:15]2[C:6]([N:7]3[C:12]([CH2:13][O:14]2)=[N:11][NH:10][C:9](=[O:17])[CH:8]3[CH3:18])=[CH:5][C:4]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 99421632-Amino-5-methoxyphenolHCID 86727481HCID 86727481, compound

Product 1

HCID 86727480HCID 86727480, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 7-methoxy-4-methyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (prepared from 2-amino-5-methoxyphenol using the similar procedure detailed in Example #56, Step A-D and Example #106, Step A, 1 g, 3.42 mmol) and lithium chloride (0.44 g, 10.27 mmol) in DMF (10 mL) was heated at 150° C. for 3 h. The reaction mixture was cooled to ambient temperature and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (eluting with 50% EtOAc in petroleum ether) to give 7-hydroxy-4-methyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.65 g, 68%) as a red solid. TLC (eluting with 50% EtOAc in petroleum ether) Rf=0.5.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-87b6606c888b49819bfd543367818274
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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