Water → HCID 21111552, compound

HRID 494708Notes

Reaction equation

HRID 494708 reaction equation
C([O:5][C:6](=[O:28])[C:7]1[C:12]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=2[Cl:21])=[C:11]([Cl:22])[C:10]([NH:23][CH2:24][C:25](=O)[CH3:26])=[N:9][CH:8]=1)(C)(C)C.OS(O)(=O)=O.O.[OH-].[Na+]>CCOC(C)=O>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:12]2[C:7]([C:6]([OH:5])=[O:28])=[CH:8][N:9]3[C:25]([CH3:26])=[CH:24][N:23]=[C:10]3[C:11]=2[Cl:22])=[C:15]([Cl:21])[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 58886660HCID 58886660, compound

Product 1

HCID 21111552HCID 21111552, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(4-Bromo-2-chlorophenylamino)-5-chloro-6-(2-oxopropylamino)-nicotinic acid tert-butyl ester (0.075 g, 0.15 mmol) was dissolved into concentrated H2SO4 (0.50 mL). After ten minutes, ice and water were and the mixture was stirred for ten minutes. The mixture was diluted with EtOAc, neutralized with 1 M NaOH, washed with brine, dried over Na2SO4 and concentrated to provide the desired product as an off-white solid. MS APCI (+) m/z 416, 418 (M+, Cl, Br pattern) detected.

Workup

  1. waitAfter ten minutes
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e63feb10c38c4d71a78b30ed77480042
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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