Sodium Hydroxide → HCID 67079883, compound

HRID 453397Notes

Reaction equation

HRID 453397 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=1[F:22])[C:10](=[O:23])[NH:9][CH2:8]2)=[O:4].[OH-].[Na+]>>[F:22][C:16]1[CH:17]=[C:18]([I:21])[CH:19]=[CH:20][C:15]=1[NH:14][C:13]1[CH:12]=[C:11]2[C:7]([CH2:8][NH:9][C:10]2=[O:23])=[CH:6][C:5]=1[C:3]([OH:4])=[O:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 67079829HCID 67079829, compound

Product 1

HCID 67079883HCID 67079883, compoundYield 116.6%

Conditions

Temperature
60 °C

Procedure

To a suspension of 6-(2-fluoro-4-iodo-phenylamino)-1-oxo-2,3-dihydro-1H-isoindole-5-carboxylic acid methyl ester (220 mg, 0.52 mmol) in IMS (7 mL) was added aqueous sodium hydroxide solution (1.3 mL, 1M, 1.30 mmol). The reaction mixture was heated at 60° C. for 3 hours, during which the solids dissolved. The reaction mixture was concentrated in vacuo to remove the IMS and the resultant solution was acidified to pH ˜5 by addition of aqueous hydrochloric acid (1M) causing a precipitate to form. The product was collected by filtration and dried under vacuum at 45° C. to yield the title compound as a brown solid (250 mg, >100%). LCMS (Method B): RT=3.07 min, M+MeCN+H+=454.

Workup

  1. dissolutiondissolved
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto remove the IMS
  4. additionthe resultant solution was acidified to pH ˜5 by addition of aqueous hydrochloric acid (1M)
  5. customto form
  6. filtrationThe product was collected by filtration
  7. customdried under vacuum at 45° C.

Sources & evidence

ORD record
ord-0043fa6c4dfe4d9ab3754a7643cd78b4
Source dataset
uspto-grants-2013_07
Patent number
US08492427B2

Reaction notes

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