Sulfuric Acid → HCID 14814852, compound

HRID 1960113Notes

Reaction equation

HRID 1960113 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-fe4d7a7ce46d4a9480adc6f27919bf13
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

Loading…