Diazomethane → Methyl 2-amino-3-iodobenzoate

HRID 1470639Notes

Reaction equation

HRID 1470639 reaction equation
[NH2:1][C:2]1[C:10]([I:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+](=[CH2:14])=[N-]>CO.C(OCC)C>[CH3:14][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([I:11])[C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 2820702-Amino-3-iodobenzoic acid

Product 1

HCID 21258150Methyl 2-amino-3-iodobenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-amino-3-iodo-benzoic acid (2.5 g, 9.5 mmol) in methanol and diethyl ether mixture (15 mL, 8:2) was added a freshly prepared solution of diazomethane gas in diethyl ether until all the starting material is consumed. Reaction mixture was then evaporated under reduced pressure to obtain a yellow solid which was purified by flash column using. 5% ethylacetate in hexane as an eluent. 1.5 g of the required product was isolated as a yellow viscous liquid.

Workup

  1. customis consumed
  2. customReaction mixture
  3. customwas then evaporated under reduced pressure
  4. customto obtain a yellow solid which
  5. customwas purified by flash column

Sources & evidence

ORD record
ord-a45cb8be52f34788823b7393a5210b19
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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