3-Nitrophenylboronic Acid → HCID 69329102, compound

HRID 1593757Notes

Reaction equation

HRID 1593757 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[Cl:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][C:14]=1[F:15])N.[N+:16](C1C=C(B(O)O)C=CC=1)([O-])=O>C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:3]([C:1]#[N:2])[C:4]([NH2:16])=[O:6])[CH:12]=[CH:13][C:14]=1[F:15]

Participants

5

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 97083-Chloro-4-fluoroanilineHCID 9740Cyanoacetic acid

Product 1

HCID 69329102HCID 69329102, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 500-mL round bottomed flask under N2 equipped with overhead stirrer, a Dean-Stark trap and condenser, thermocouple was charged with cyanoacetic acid (28.04 g, 0.33 mol), 3-chloro-4-fluoroaniline (40.0 g, 0.28 mol), 3-nitrophenylboronic acid (2.28 g, 0.014 mol) and toluene (200 mL). The mixture was heated to reflux and water collected in the Dean-Stark trap. After 5.5 hours, thin layer chromatography (TLC) indicated complete consumption of the aniline. The reaction mixture was cooled to room temperature (RT) forming a pink suspension. The solids were isolated by filtration, washed with MTBE (2×200 mL) and dried to afford (3-chloro-4-fluorophenyl)-2-cyanoacetamide as a pale pink solid (46.40 g, 79% yield, 96.7% by GC-MS). 1H NMR (300 MHz, DMSO-d6): 10.4 (s, 1H), 7.80 (d, J=8 Hz, 1H), 7.5-7.3 (m, 2H), 3.92 (s, 2H).

Workup

  1. customA 500-mL round bottomed flask under N2 equipped with overhead stirrer
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. customwater collected in the Dean-Stark trap
  5. customconsumption of the aniline
  6. customforming a pink suspension
  7. customThe solids were isolated by filtration
  8. washwashed with MTBE (2×200 mL)
  9. customdried

Sources & evidence

ORD record
ord-e481a28cfb0b42778403959fcd8fd134
Source dataset
uspto-grants-2007_11
Patent number
US07297795B2

Reaction notes

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