Methyl 3-amino-5-chloro-2-hydroxybenzoate → HCID 59497315, compound

HRID 1747464Notes

Reaction equation

HRID 1747464 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([NH2:11])[C:5]=1[OH:12].[C:14](C1NC=CN=1)(C1NC=CN=1)=[O:15]>O1CCCC1>[CH3:1][O:2][C:3]([C:4]1[C:5]2[O:12][C:14](=[O:15])[NH:11][C:6]=2[CH:7]=[C:8]([Cl:10])[CH:9]=1)=[O:13]

Participants

4

Reactant 2

HCID 687991Methyl 3-amino-5-chloro-2-hydroxybenzoateHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 59497315HCID 59497315, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-5-chloro-2-hydroxy-benzoic acid methyl ester 8 g (39.6 mmol) is dissolved in tetrahydrofuran 100 mL and carbonyl diimidazole (12.9 g, 79.3 mmol) is added. The reaction is heated to reflux for 2 hours and then cooled to room temperature. The reaction is evaporated in vacuo and then taken up in dichloromethane (200 mL) and then washed with HCl (2N, 50 mL 2×) and water (2×50 mL). The organic layer is dried (Na2SO4) filtered and evaporated in vacuo to give the title compound (8.2 g, 36 mmol, 91%). LCMS (ESMS): m/z 228.9 (M+H+).

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux for 2 hours
  3. customThe reaction is evaporated in vacuo
  4. washwashed with HCl (2N, 50 mL 2×) and water (2×50 mL)
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-e096262db25241c095bc3bd2220412e7
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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