Sulfuric Acid → HCID 14814852, compound

HRID 1945274Notes

Reaction equation

HRID 1945274 reaction equation
N[C:2]1[C:3]([CH3:13])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[OH:14]S(O)(=O)=O.N([O-])=O.[Na+]>O>[OH:14][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 46835529Methyl 5-amino-2,4-dimethylbenzoate

Product 1

HCID 14814852HCID 14814852, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Methyl 5-amino-2,4-dimethylbenzoate (0.752 g, 4.20 mmol) in 5 mL water was cooled with an ice bath. H2SO4 (1.1 mL, 21 mmol) was added followed by a solution of sodium nitrite (0.301 g, 4.4 mmol) in 3 mL of water. The reaction was stirred in an ice bath for 30 min, and then in a 100° C. oil bath for 60 min. The reaction was cooled to rt and partitioned between EtOAc and brine. The organic phase was dried (Na2SO4) and concentrated to give the title compound as a yellow oil. 1H NMR (CDCl3) δ 7.48 (s, 1H), 7.00 (s, 1H), 5.95 (bs, 1H), 3.90 (s, 3H), 2.50 (s, 3H), 2.28 (s, 3H).

Workup

  1. waitin a 100° C. oil bath for 60 min
  2. custompartitioned between EtOAc and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8c44e6d8c6664d259478ab7860faa177
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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