Potassium Carbonate → HCID 43082674, compound

HRID 1184422Notes

Reaction equation

HRID 1184422 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].Br[CH2:14][C:15]([O:17][CH3:18])=[O:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 181694-Hydroxy-3-nitrobenzaldehydeHCID 60984Methyl bromoacetate

Product 1

HCID 43082674HCID 43082674, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a 200 mL round-bottomed flask was added 4-hydroxy-3-nitrobenzaldehyde (1.671 g, 10.0 mmol), methyl 2-bromoacetate (0.950 mL, 10.00 mmol), and K2CO3 (1.382 g, 10.00 mmol) in DMF (25 mL). The reaction was stirred at 80° C. for 2 hr. The reaction was poured over ice and the resulting solid was isolated by filtration, washed with water and dried in vacuo to give a light yellow solid (2.031 g, 85% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.71 (s, 3H) 5.18 (s, 2H) 7.52 (d, J=8.84 Hz, 1 H) 8.14 (dd, J=8.84, 2.02 Hz, 1H) 8.44 (d, J=2.02 Hz, 1H) 9.95 (s, 1H). ESI-MS: m/z 240.1 (M+H)+.

Workup

  1. additionThe reaction was poured over ice
  2. customthe resulting solid was isolated by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c2f586e29f7a475e867257707d1dd27a
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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