Hydrochloric Acid → HCID 22648899, compound

HRID 843707Notes

Reaction equation

HRID 843707 reaction equation
CC([N:5]([C:9]1[CH:10]=[CH:11][C:12]2[NH:17]C(=O)[O:15][C:14](=[O:19])[C:13]=2[C:20]=1[CH3:21])[C:6](=[O:8])[O-:7])(C)C.[OH-].[Na+].Cl>CC(C)=O>[NH2:17][C:12]1[CH:11]=[CH:10][C:9]([NH:5][C:6]([O:7][C:13]([CH3:20])([CH3:14])[CH3:12])=[O:8])=[C:20]([CH3:21])[C:13]=1[C:14]([OH:15])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23444334HCID 23444334, compound

Product 1

HCID 22648899HCID 22648899, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of the product of step C ((10.5 g, 36.0 mmol) in 15 mL of acetone was added 107 mL of 1N NaOH. After stirring at room temperature for 1 hour, the solution was acidified to pH 3 by the careful addition of 2N HCl. The mixture was extracted (2×) with EtOAc, dried (MgSO4), and concentrated under reduced pressure affording 8.35 g (87%) of 2-amino-5-[[(1,1-dimethylethoxy]carbonyl]amino]-6-methylbenzoic acid: Anal. Calc'd. for C13H18N2O4: C, 58.64; H, 6.81; N, 10.52. Found: C, 58.26; H, 6.72; N, 10.42.

Workup

  1. extractionThe mixture was extracted (2×) with EtOAc
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-54acc9f6509443fe90501b4138062713
Source dataset
uspto-grants-2002_04
Patent number
US06380189B1

Reaction notes

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