Methyl Anthranilate → HCID 11805118, compound

HRID 659648Notes

Reaction equation

HRID 659648 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N:12]([O-])=O.[Na+].O.O.Cl[Sn]Cl>Cl.O>[NH:1]([C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[NH2:12]

Participants

6

Reactant 3

HCID 8635Methyl AnthranilateHCID 61436Stannous chloride dihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 11805118HCID 11805118, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A 100-mL round-bottom flask was a solution of methyl 2-aminobenzoate (1 g, 6.62 mmol, 1.00 equiv) in HCl (30%, 10 mL). To this solution was added a solution of NaNO2 (500 mg, 7.25 mmol, 1.02 equiv) in H2O (10 mL) dropwise at 0° C. over 5 minutes. The resulting mixture was stirred at 0° C. for 30 minutes. Then, a solution of SnCl2.2H2O (2.75 g, 12.19 mmol, 2.00 equiv) in HCl (30%) (12 mL) was added dropwise at 0° C. The resulting solution was stirred for an additional 2 hours at room temperature. The solids were collected by filtration and washed with H2O (2×20 mL) affording methyl 2-hydrazinylbenzoate as white solid (0.6 g, 55%).

Workup

  1. customA 100-mL round-bottom flask was
  2. stirringThe resulting solution was stirred for an additional 2 hours at room temperature
  3. filtrationThe solids were collected by filtration
  4. washwashed with H2O (2×20 mL)

Sources & evidence

ORD record
ord-0fc0d9e94c054a318734335dfd15f83c
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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