Tetrahydrofuran → 2-Amino-3-phenyl-6-(carboxy)imidazo[1,2-a]pyridine

HRID 277928Notes

Reaction equation

HRID 277928 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10]([O:12]C)=[O:11])=[CH:6][N:5]2[C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.[OH-].[Li+].C1COCC1>O>[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6][N:5]2[C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 226266722-Amino-3-phenyl-6-(carbomethoxy)imidazo-[1,2-a]-pyridine

Product 1

HCID 226267402-Amino-3-phenyl-6-(carboxy)imidazo[1,2-a]pyridineYield 101.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 2-amino-3-phenyl-6-(carbomethoxy)imidazo-[1,2-a]-pyridine (83.9 g, 0.314 mol), lithium hyroxide monohydrate (65.9 g, 1.57 mol), 1113 ml of THF, and 371 ml of H2O were combined and stirred for 18 hours at RT. The reaction was concentrated in vacuo and the residue taken up in 5 L of H2O. The pH was adjusted to 5 with 5N HCl. The resulting precipitate was filtered and air dried for 72 hours to give 80.5 g of product. (quant. yeild). NMR, MS(FD).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. filtrationThe resulting precipitate was filtered
  3. customair dried for 72 hours

Sources & evidence

ORD record
ord-b9cf1971e2c1413bb796d9780121a133
Source dataset
uspto-grants-2002_03
Patent number
US06358971B1

Reaction notes

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