Hydrochloric Acid → HCID 15283177, compound

HRID 22185Notes

Reaction equation

HRID 22185 reaction equation
[N+:1]([C:4]1[C:5]([CH2:15][CH3:16])=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9]C(=O)[C:7]2=[O:14])([O-:3])=[O:2].[OH:17]O.Cl>[OH-].[Na+]>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([NH2:9])=[C:6]([C:5]=1[CH2:15][CH3:16])[C:7]([OH:14])=[O:17])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 152831765-Nitro-4-ethylisatin

Product 1

HCID 15283177HCID 15283177, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 1.0 g (4.5 mmoles) of 5-nitro-4-ethylisatin in 8.0 mL of 5% NaOH was slowly added 1.25 mL (11 mmoles) of 30% hydrogen peroxide over 10 minutes. A mild exotherm was detectable. The solution was stirred at room temperature for 60 minutes, then poured over crushed ice. The solution was acidified with 10% HCl until the `cloud point`. The suspension was extracted 3× with ethyl acetate. The combined organic extracts were washed 1× with water, dried over MgSO4, and concentrated in vacuo. There was obtained a dark oil, which upon standing at room temperature, became an orange-rust colored solid. 0.78 g (82% yield) of 5-nitro-6-ethyl-2-aminobenzoic acid was obtained. NMR(DMSO-d6): 1.16(t,3H,J=7.2 Hz), 2.88(q,2H,J=7.2 Hz), 3.34(bs,2H), 6.66(d,1H,J=9.3 Hz), 7.84(d,1H,J=9.3 Hz). MS(m/z): 210(M+).

Workup

  1. customover 10 minutes
  2. additionpoured
  3. customover crushed ice
  4. extractionThe suspension was extracted 3× with ethyl acetate
  5. washThe combined organic extracts were washed 1× with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThere was obtained a dark oil, which
  9. customupon standing at room temperature

Sources & evidence

ORD record
ord-1a2558a25c3149839e0db0e3cae5a089
Source dataset
uspto-grants-1995_06
Patent number
US05428021

Reaction notes

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