Hydrochloric Acid → HCID 89120830, compound

HRID 1908952Notes

Reaction equation

HRID 1908952 reaction equation
N([O-])=O.[Na+].[CH3:5][O:6][C:7]1[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[C:10]([NH2:17])=[CH:9][C:8]=1[O:18][CH3:19].Cl.[N-:21]=[N+:22]=[N-].[Na+].C([O-])(=O)C.[Na+]>O>[N:17]([C:10]1[CH:9]=[C:8]([O:18][CH3:19])[C:7]([O:6][CH3:5])=[CH:12][C:11]=1[C:13]([O:15][CH3:16])=[O:14])=[N+:21]=[N-:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 517045Sodium AcetateHCID 611144Methyl 4,5-dimethoxyanthranilateHCID 23668193Sodium Nitrite

Product 1

HCID 89120830HCID 89120830, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (486 mg, 7.1 mmol) in H2O (6 mL) was added to a solution of methyl 2-amino-4,5-dimethoxy benzoate (1.0 g, 4.7 mmol) in 6N—HCl (20 mL) at 0° C. under N2 atmosphere. After stirring for 15 min, the mixture was then added dropwise to a stirred solution of sodium azide (611 mg, 9.4 mmol) and sodium acetate (3.86 g, 47 mmol) in H2O (30 mL) at 0° C. under N2 atmosphere. After the addition was completed, the reaction mixture was warmed to room temperature and stirred for 2 hrs. The resulting precipitate was collected by vacuum filtration, wash with cold water and dried under reduced pressure to yield methyl 2-azido-4,5-dimethoxybenzoate (909 mg, 82%). 1H NMR (CDCl3, 600 MHz) δ 7.42 (s, 1H), 6.66 (s, 1H), 3.95 (s, 3H), 3.90 (s, 6H); MS (ES+) m/z 238.2 (M+H)+

Workup

  1. additionAfter the addition
  2. stirringstirred for 2 hrs
  3. filtrationThe resulting precipitate was collected by vacuum filtration
  4. washwash with cold water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-41b661c02ec64bcca42a8ebcc6d7e0e9
Source dataset
uspto-grants-2013_12
Patent number
US08598342B2

Reaction notes

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