Chlorosuccinimide → Methyl 3-amino-6-chloro-2-methylbenzoate

HRID 650905Notes

Reaction equation

HRID 650905 reaction equation
[NH2:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1C(=O)N([Cl:20])C(=O)C1>CN(C=O)C>[NH2:1][C:2]1[C:3]([CH3:12])=[C:4]([C:9]([Cl:20])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 38010253-Amino-2-methylbenzoic acid methyl ester

Product 1

HCID 21710154Methyl 3-amino-6-chloro-2-methylbenzoateYield 40.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared in a manner analogous to Step C, Example 1. Here, 29.9 grams (0.181 mole) of methyl 3-amino-2-methylbenzoate was combined with 27.8 grams (0.208 mole) of NCS in 800 mL of DMF. The reaction product was purified by column chromatography on silica gel using mixtures of EtOAc and hexane as eluants. The fractions containing product were combined and concentrated under reduced pressure, yielding 14.7 grams of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to Step C, Example 1
  2. customThe reaction product was purified by column chromatography on silica gel using mixtures of EtOAc and hexane as eluants
  3. additionThe fractions containing product
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-937fb27df42443a789ec87734425fc94
Source dataset
uspto-grants-2001_08
Patent number
US06277847B1

Reaction notes

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