Potassium Carbonate → HCID 10172277, compound

HRID 856948Notes

Reaction equation

HRID 856948 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][OH:12])=[CH:6][C:3]=1[C:4]#[N:5].Cl[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:5][C:4]1[C:3]2[CH:6]=[C:7]3[C:8]([O:12][CH2:11][O:10]3)=[CH:9][C:2]=2[O:1][C:14]=1[C:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 202502,2',4'-TrichloroacetophenoneHCID 21864975HCID 21864975, compound

Product 1

HCID 10172277HCID 10172277, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-hydroxy-5-hydroxymethoxy-benzonitrile (0.10 g, 0.61 mmol), 2,2′,4′-trichloroacetophenone (0.16 g, 0.74 mmol, 1.2 eq) and potassium carbonate (0.13 g, 0.92 mmol, 1.5 eq) in 1 mL DMF was stirred overnight at 80° C. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried with sodium sulfate and filtered through a plug of silica. Concentration in vacuo provided an orange solid, purification of which by RP-HPLC (H2O-MeCN gradient) provided 0.13 g (61%) of (7-amino-1,3,5-trioxa-s-indacen-6-yl)-(2,4-dichloro-phenyl)-methanone as a yellow solid. 1H-NMR (DMSO-d6) δ 7.70–7.69 (m, 1 H), 7.51–7.49, (m 2H), 7.42, (s, 1H) 7.30 (bs, 2H), 7.03 (s, 1H), 6.07 (s, 2H); MS LC-MS (MH+=350.2/352.1), LC-MS RT=3.21 min.

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered through a plug of silica
  6. concentrationConcentration in vacuo
  7. customprovided
  8. customan orange solid, purification of which by RP-HPLC (H2O-MeCN gradient)

Sources & evidence

ORD record
ord-b87e1e501ade41b69627680b00486f48
Source dataset
uspto-grants-2006_12
Patent number
US07144885B2

Reaction notes

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