Sodium Hydroxide → 8-(trans-2,3-Dihydro-2-hydroxy-1-indenylamino)-2,3-dimethyl-imidazo[1,2-a]pyridine-6-carboxylic acid

HRID 2053034Notes

Reaction equation

HRID 2053034 reaction equation
[OH:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[NH:11][C:12]1[C:13]2[N:14]([C:22]([CH3:26])=[C:23]([CH3:25])[N:24]=2)[CH:15]=[C:16]([C:18]([O:20]C)=[O:19])[CH:17]=1.[OH-].[Na+]>O1CCOCC1>[OH:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[NH:11][C:12]1[C:13]2[N:14]([C:22]([CH3:26])=[C:23]([CH3:25])[N:24]=2)[CH:15]=[C:16]([C:18]([OH:20])=[O:19])[CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69114655Methyl 8-(trans-2,3-dihydro-2-hydroxy-1-indenylamino)-2,3-dimethyl-imidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 691143868-(trans-2,3-Dihydro-2-hydroxy-1-indenylamino)-2,3-dimethyl-imidazo[1,2-a]pyridine-6-carboxylic acidYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.0 g (5.7 mmol) methyl 8-(trans-2,3-dihydro-2-hydroxy-1-indenylamino)-2,3-dimethyl-imidazo[1,2-a]pyridine-6-carboxylate are suspended in 100 ml dioxane and 20 ml 2N aqueous sodium hydroxide and heated to reflux. After 1 h the reaction mixture is cooled down, evaporated in vacuo to ¼ of its volume and 50 ml water are added. The pH of the mixture is adjusted to pH=7 by adding 2N hydrochloric acid and the flask is placed in an ice bath. After 30 min, the precipitate is collected, washed with water and dried in vacuo at 50° C. to yield 1.4 g (73%) of the title compound (m.p. 246-249° C.).

Workup

  1. temperatureAfter 1 h the reaction mixture is cooled down
  2. customevaporated in vacuo
  3. additionare added
  4. additionby adding 2N hydrochloric acid
  5. customthe flask is placed in an ice bath
  6. customthe precipitate is collected
  7. washwashed with water
  8. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-d101d1924c994a148e0bd10639dea45d
Source dataset
uspto-grants-2008_02
Patent number
US07326718B2

Reaction notes

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