Potassium Carbonate → HCID 178487567, compound

HRID 2206285Notes

Reaction equation

HRID 2206285 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[C:9]([CH:10]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=3)[C:11]=1[C:12]#[N:13])=[CH:8][CH:7]=[C:6]1[CH:25]=[CH:26][CH:27]=[CH:28][C:5]=21.Cl.[NH2:30][OH:31].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C>[NH2:1][C:2]1[O:3][C:4]2[C:9]([CH:10]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=3)[C:11]=1[C:12]([NH:30][OH:31])=[NH:13])=[CH:8][CH:7]=[C:6]1[CH:25]=[CH:26][CH:27]=[CH:28][C:5]=21

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 9803111HCID 9803111, compound

Product 1

HCID 178487567HCID 178487567, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-4-(3-bromo-4,5-dimethoxy-phenyl)-4H-benzo[h]chromene-3-carbonitrile (1) (4.38 g, 10 mmol), hydroxylamine hydrochloride (2.80 g, 40 mmol) and potassium carbonate (2.80 g, 1 mmol) were suspended in 80 ml ethanol at room temperature then stirred under LC-MS control 48 h. The reaction was clean with a minor side product (<3%). The reaction mixture was diluted with ethyl acetate to about 150 ml and stirred for 2 h at room temperature. Thus resulting insoluble salt was separated by filtration, washed well with ethyl acetate and the combined organic solution was evaporated to dryness at 40° C. under vacuum and the residue was dried under high vacuum to get solids (4.70 g, 10 mmol, 100% theoretical yield) of the title compound.

Workup

  1. stirringstirred for 2 h at room temperature
  2. customThus resulting insoluble salt was separated by filtration
  3. washwashed well with ethyl acetate
  4. customthe combined organic solution was evaporated to dryness at 40° C. under vacuum
  5. customthe residue was dried under high vacuum
  6. customto get

Sources & evidence

ORD record
ord-555ca438d1a34117b6b27c063fea85dd
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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