Hydrochloric Acid → HCID 86652839, compound

HRID 1188900Notes

Reaction equation

HRID 1188900 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][N:14]=2)[CH:9]=[CH:8][C:6]=1[NH2:7])[CH3:3].Cl.[N:24]([O-])=O.[Na+].[CH3:28][CH:29](C(=O)C)[C:30]([O:32][CH2:33][CH3:34])=[O:31].[OH-].[K+]>C(#N)C.C(O)C.O>[CH3:3][CH:2]([O:4][C:5]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:15][N:14]=2)[CH:9]=[CH:8][C:6]=1[NH:7][N:24]=[C:29]([CH3:28])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:1]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 701Ethyl 2-methylacetoacetateHCID 14797Potassium HydroxideHCID 23668193Sodium NitriteHCID 67118502HCID 67118502, compound

Product 1

HCID 86652839HCID 86652839, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
-5 °C

Procedure

To a stirring suspension of 2-(1-methylethoxy)-4-{[5-(methylsulfonyl)pyridin-2-yl]oxy}aniline (32 g) in a mixture of acetonitrile (50 mL) and ethanol (100 mL) was added a concentrated hydrochloric acid (30 mL) at 0° C. After cooling to −5° C., a solution of sodium nitrite (8.2 g) in water (25 mL) was added dropwise to the mixture with keeping the temperature. below 0° C. The mixture was stirred at −10 to −5° C. for 30 min. The mixture was added to a mixture of ethyl 2-methyl-3-oxobutanoate (15.7 mL), potassium hydroxide (85%, 26 g), ethanol (140 mL) and water (140 mL) at −40 to −30° C. over 30 min. After stirring at −38° C. for 1 h, the resulting orange suspension was filtered to give the title compound as a wet orange solid. MS 434 (MH+).

Workup

  1. custombelow 0° C
  2. stirringAfter stirring at −38° C. for 1 h
  3. filtrationthe resulting orange suspension was filtered

Sources & evidence

ORD record
ord-8a60cdb7c2ac482e8f6807f1927e1a87
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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