Methanol → Methyl 5-Amino-2-chlorobenzoate

HRID 1790279Notes

Reaction equation

HRID 1790279 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=1[Cl:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 378795-Amino-2-chlorobenzoic acid

Product 1

HCID 5200412Methyl 5-Amino-2-chlorobenzoate

Procedure

To a slurry of 5-amino-2-chloro-benzoic acid (20.0 g, 0.12 mol) in methanol (150 mL) was added concentrated sulfuric acid (25 mL). The resulting reaction was heated at reflux for 4 hours, cooled, and concentrated in vacuo. The residual was taken up in water and neutralized with Na2CO3. The aqueous was extracted with CH2Cl2 (3×). The organics were dried over sodium sulfate and concentrated in vacuo to yield the above named compound (14.0 g).

Workup

  1. customThe resulting reaction
  2. temperaturewas heated
  3. temperatureat reflux for 4 hours
  4. temperaturecooled
  5. concentrationconcentrated in vacuo
  6. extractionThe aqueous was extracted with CH2Cl2 (3×)
  7. dry with materialThe organics were dried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4fb685667cc4027a9ae52d41dc084f1
Source dataset
uspto-grants-2006_07
Patent number
US07071223B1

Reaction notes

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