Potassium Hydroxide → 4-(3-Methoxyphenyl)thiophen-2-amine

HRID 573564Notes

Reaction equation

HRID 573564 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[C:6]=1C(OCC)=O.[OH-].[K+]>C(O)C>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([C:5]2[CH:6]=[C:2]([NH2:1])[S:3][CH:4]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 690667Ethyl 2-amino-4-(3-methoxyphenyl)thiophene-3-carboxylate

Product 1

HCID 672362194-(3-Methoxyphenyl)thiophen-2-amineYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 2-amino-4-[3-(methyloxy)phenyl]-3-thiophene carboxylate (Description 39) (5 g, 18.03 mmol) and 20% aqueous solution of potassium hydroxide (100 mL, 18.03 mmol) in ethanol (100 mL) was heated at 110° C. for 24 h. After cooling to RT the ethanol was removed under reduced pressure. The residue was poured into water (100 mL) and extracted with ethyl acetate (50 mL×3). The organic layers were combined, washed with brine (100 mL), dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with a gradient of 0-25% ethyl acetate in cyclohexane, to give the title compound (1.83 g). LCMS (A) m/z: 206 [M+1]+, Rt 1.14 min (acidic).

Workup

  1. customwas removed under reduced pressure
  2. additionThe residue was poured into water (100 mL)
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. washwashed with brine (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by chromatography on silica
  9. washeluting with a gradient of 0-25% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-d8b1ef6b7dc54d4bbfc6b99244fc0cc5
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

Loading…