Hydrochloric Acid → HCID 59726101, compound

HRID 336428Notes

Reaction equation

HRID 336428 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[OH:15].[C:16]([O-])([O-])=O.[K+].[K+].IC.Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[O:15][CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 106584324,6-dichloro-3-hydroxy-2-nitrobenzoic acid

Product 1

HCID 59726101HCID 59726101, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of acid 1-6 (0.88 g, 3.5 mmol) in DMF (8 mL) was added K2CO3 (1.44 g, 10 mmol) followed by iodomethane (0.43 mL, 6.95 mmol). The reaction was heated to 60° C. for 17 h then DMF was removed under reduced pressure to give an orange gum. H2O (20 mL) was added and the solution was acidified to pH 1 with a 10% HCl solution. The aqueous solution was then extracted with EtOAc (30 mL) and washed with H2O and brine. After drying over Na2SO4 the reaction was filtered and concentrated to afford 1-7 as an orange gum (0.82 g, 88% yield). 1H NMR (400 MHz, CDCl3) δ 3.94 (s, 3H), 7.69 (s, 1H), 10.85 (br s, 1H).

Workup

  1. customDMF was removed under reduced pressure
  2. customto give an orange gum
  3. extractionThe aqueous solution was then extracted with EtOAc (30 mL)
  4. washwashed with H2O and brine
  5. dry with materialAfter drying over Na2SO4 the reaction
  6. filtrationwas filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6cbfdab896644684a77bab73235d9c01
Source dataset
uspto-grants-2014_11
Patent number
US08889695B2

Reaction notes

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