Sodium Hydroxide → HCID 67219255, compound

HRID 1445602Notes

Reaction equation

HRID 1445602 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:27])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:8]=1[CH3:26]>C1COCC1.CO>[CH3:26][C:8]1[N:9]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:15]2[C:7]=1[CH2:6][C:5]([OH:27])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67218923HCID 67218923, compound

Product 1

HCID 67219255HCID 67219255, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1M Aqueous NaOH (1.18 ml) is added to a stirring suspension of [2-methyl-1-(4-nitro-benzyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (0.2 g, 0.54 mmol) in 4:1 THF/MeOH (5 ml). The reaction mixture is allowed to stir at room temperature for 4 hours and then the solvent is removed in vacuo. The crude residue is dissolved in 1:1 THF/water and acidified to pH 3-4 using 6M HCl. After stirring for 30 minutes the resulting suspension is filtered and dried in vacuo at 110° C. to yield the titled product as a yellow solid. (MH+ 326)

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe crude residue is dissolved in 1:1 THF/water
  3. stirringAfter stirring for 30 minutes the resulting suspension
  4. filtrationis filtered
  5. customdried in vacuo at 110° C.

Sources & evidence

ORD record
ord-d9acd74785854bfab18d8ed80db2b939
Source dataset
uspto-grants-2010_02
Patent number
US07666878B2

Reaction notes

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