Potassium Carbonate → HCID 10172277, compound

HRID 131166Notes

Reaction equation

HRID 131166 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-58004caf435d4f82991331883e49717d
Source dataset
uspto-grants-2008_06
Patent number
US07384947B2

Reaction notes

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