Sodium Hydroxide → HCID 59608227, compound

HRID 2384066Notes

Reaction equation

HRID 2384066 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16](=[O:18])[NH2:17])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[OH-].[Na+]>CO>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:12]([O:14][CH2:15][C:16](=[O:18])[NH2:17])[CH:13]=[C:4]([C:3]([OH:19])=[O:2])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67506130HCID 67506130, compound

Product 1

HCID 59608227HCID 59608227, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Next, to a solution of 5-carbamoylmethoxyisophthalic acid dimethyl ester (371 mg, 1.39 mmol) in MeOH (10 mL) is added aqueous 1M NaOH (1.39 mL, 1.39 mmol) and the mixture is stirred at 50° C. for 18 hours. The solvent is removed under reduced pressure and water is added to the residue. The aqueous solution is acidified with aqueous 1M HCl and the resulting precipitate is filtered, washed with water and dried under reduced pressure to give 5-carbamoylmethoxyisophthalic acid monomethyl ester. MS 254.3 (M+1); 1H-NMR (400 MHz, DMSO-d6); δ ppm 3.89 (s, 3H), 4.59 (s, 2H), 7.43 (s, 1H), 7.70 (m 3H), 8.10 (s, 1), 13.38 (s, 1H).

Workup

  1. customThe solvent is removed under reduced pressure and water
  2. additionis added to the residue
  3. filtrationthe resulting precipitate is filtered
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-bd2dac8e767242a492c506fb263ebcf6
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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