Tetrahydrofuran → Formic acid (2-formylamino-5-methoxybenzyl)ester

HRID 350608Notes

Reaction equation

HRID 350608 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][OH:11].C([CH2:14][O:15]C=O)#N.[O:18]1CCC[CH2:19]1>>[CH:14]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][O:11][CH:19]=[O:18])=[O:15]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4205685(Formyloxy)acetonitrileHCID 13756678(2-Amino-5-methoxyphenyl)methanol

Product 1

HCID 86596179Formic acid (2-formylamino-5-methoxybenzyl)ester

Conditions

Temperature
0 °C

Procedure

A solution of 7.00 g of (2-amino-5-methoxyphenyl)methanol, 9.8 ml of formic acid cyanomethyl ester and 0.05 g of 4-N,N-(dimethylamino)pyridine in 30 ml of anhydrous tetrahydrofuran was heated for 5 hours under reflux. The solution was then concentrated by evaporation in vacuo and the residue was taken up in 100 ml of ethyl acetate. Crystals formed on cooling the solution to 0° C., which were suction filtered, washed with methanol, and dried in vacuo. 7.20 g (75% of theory) of the title compound were thereby obtained.

Workup

  1. temperatureunder reflux
  2. concentrationThe solution was then concentrated by evaporation in vacuo
  3. customCrystals formed
  4. filtrationfiltered
  5. washwashed with methanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-277ff5e3f8794036a77bcf51628f651d
Source dataset
uspto-grants-2007_02
Patent number
US07183274B2

Reaction notes

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