Sodium Hydroxide → HCID 21696635, compound

HRID 378801Notes

Reaction equation

HRID 378801 reaction equation
C[C:2]1[C:3]([NH2:21])=[C:4]([Cl:20])[C:5]([C:17]([OH:19])=[O:18])=[N:6][C:7]=1[O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1.[OH-].[Na+]>CO>[NH2:21][C:3]1[CH:2]=[C:7]([O:8][C:9]2[CH:10]=[C:11]([Cl:16])[CH:12]=[C:13]([Cl:15])[CH:14]=2)[N:6]=[C:5]([C:17]([OH:19])=[O:18])[C:4]=1[Cl:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21696656HCID 21696656, compound

Product 1

HCID 21696635HCID 21696635, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To Methyl 4-amino-3-chloro-6-(3,5-dichlorophenoxy)pyridine-2-carboxylic acid (0.0.720 g, 2.07 mmol) in 20 mL of methanol was added 1N NaOH (2.07 mL) and stirred at RT for 1 hr. The reaction mixture was concentrated to dryness in vacuo and 100 mL each of diethyl ether and H2O added. The aqueous layer acidified with 1N HCl until pH=2. Methylene chloride was added and the aqueous phase was extracted with additional CH2Cl2 (2×100 mL). The combined extracts were dried (MgSO4) and concentrated to dryness in vacuo to give 0.390 g of white solid 4-amino-3-chloro-6-(3,5-dichlorophenoxy)pyridine-2-carboxylic acid (Compound 47); mp 196° C.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness in vacuo and 100 mL each of diethyl ether and H2O
  2. additionadded
  3. additionMethylene chloride was added
  4. extractionthe aqueous phase was extracted with additional CH2Cl2 (2×100 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-a7bca18f484b44e1a5621eaa403d2f0b
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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