3,4-Dimethoxyaniline → HCID 64280908, compound

HRID 1772921Notes

Reaction equation

HRID 1772921 reaction equation
O[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[S:8]([OH:11])(=[O:10])=O.C(N(CC)C(C)C)(C)C.O(Cl)[Cl:22].[P+5].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[NH2:30].C([O-])(O)=O.[Na+]>ClCCCl.CCOC(C)=O.CCCCCC>[Cl:22][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[S:8]([NH:30][C:29]1[CH:31]=[CH:32][C:33]([O:34][CH3:35])=[C:27]([O:26][CH3:25])[CH:28]=1)(=[O:10])=[O:11]

Participants

9

Reactant 5

HCID 227703,4-DimethoxyanilineHCID 81531Diisopropylethylamine2×HCID 516892Sodium BicarbonateHCID 178479711HCID 178479711, compoundHCID 178527631HCID 178527631, compound

Product 1

HCID 64280908HCID 64280908, compoundYield 23.5%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent2×HCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-hydroxypyridine-3-sulfonic acid (5.0 g, 28.5 mmol), N,N-diisopropylethylamine (9.2 g, 71.3 mmol), phosphorus(V) oxychloride (10.9 g, 71.3 mmol) in 1,2-dichloroethane (50 mL) was heated at 90° C. for 45 min with TLC monitoring (hexane:EtOAc, 1:1). After cooling, the solution was added to 3,4-dimethoxyaniline (4.8 g, 31.0 mmol), N,N-diisopropylethylamine (7.35 g, 57.0 mmol) in 1,2-dichloroethane (50 mL) at −10° C. and the resulting mixture stirred for approximately 2 h at rt with TLC monitoring (hexane:EtOAc, 1:1). The mixture was then added to saturated aqueous NaHCO3 (200 mL), extracted with DCM (3×50 mL) and the combined organic layers dried over Na2SO4 and concentrated in vacuo. Purification by gradient column chromatography eluting with 0-20% EtOAc in hexane yielded the title compound (2.2 g, 6.69 mmol).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with DCM (3×50 mL)
  3. dry with materialthe combined organic layers dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by gradient column chromatography
  6. washeluting with 0-20% EtOAc in hexane

Sources & evidence

ORD record
ord-e7aabb87e3e44d1687d6db9c1ee36847
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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