Hydrochloric Acid → HCID 22648899, compound

HRID 1603010Notes

Reaction equation

HRID 1603010 reaction equation
[CH3:1][C:2]1[C:7]2[C:8](=[O:13])[O:9]C(=O)[NH:11][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].[OH-].[Na+].Cl>CC(C)=O>[NH2:11][C:6]1[CH:5]=[CH:4][C:3]([NH:14][C:15]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:21])=[C:2]([CH3:1])[C:7]=1[C:8]([OH:13])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54327239HCID 54327239, 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-f200e755fd6647178fa599522455cbd7
Source dataset
uspto-grants-1999_11
Patent number
US05985872

Reaction notes

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