Sodium Carbonate → Methyl 3-[(cyclopropylamino)carbonyl]benzoate

HRID 1432121Notes

Reaction equation

HRID 1432121 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=O)[CH:5]=1.O=S(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].[CH:24]1([NH2:27])[CH2:26][CH2:25]1>CN(C=O)C.C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([NH:27][CH:24]2[CH2:26][CH2:25]2)=[O:9])[CH:5]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 6018803-(Methoxycarbonyl)benzoic acid

Product 1

HCID 47231565Methyl 3-[(cyclopropylamino)carbonyl]benzoate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 0.5 g (2.77 mmol) isophthalic acid mono methyl ester, 5 ml toluene and 0.8 ml SOCl2 is treated with one drop DMF and heated to 80° C. till the evolution of gas ceases. After cooling down the mixture is evaporated, dissolved in 2 ml DCM and added to an at 0° C. stirred mixture of 5 ml 10% aqueous Na2CO3, 0.21 ml (3.0 mmol) cyclopropyl amine and 5 ml DCM. After 1 h the layers are separated and the organic layer is washed with 1 N HCl, brine, dried with sodium sulfate and evaporated. The crude product is crystallized (EtOAc, hexane) to yield N-cyclopropyl-isophthalamic acid methyl ester as off-white crystals.

Workup

  1. temperatureAfter cooling down the mixture
  2. customis evaporated
  3. dissolutiondissolved in 2 ml DCM
  4. additionadded to an at 0° C.
  5. customAfter 1 h the layers are separated
  6. washthe organic layer is washed with 1 N HCl, brine
  7. dry with materialdried with sodium sulfate
  8. customevaporated
  9. customThe crude product is crystallized (EtOAc, hexane)

Sources & evidence

ORD record
ord-491ea11d1ce84a0191f3429805eae162
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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