2-Azidobenzoic acid → HCID 178423533, compound

HRID 856910Notes

Reaction equation

HRID 856910 reaction equation
[Na].[CH3:2][C:3]1[O:7][N:6]=[C:5]([CH2:8][C:9]#[N:10])[CH:4]=1.[N:11]([C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=O)=[N+:12]=[N-:13]>CCO>[CH3:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:13]=[N:12][N:11]3[C:14]4[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:16](=[O:18])[NH:10][C:9]=23)[CH:4]=1

Participants

5

Reactant 3

HCID 53255602-Azidobenzoic acidHCID 5360545SodiumHCID 112172525-Methyl-3-isoxazoleacetonitrile

Product 1

HCID 178423533HCID 178423533, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (0.2 g, 8.6 mmol) was dissolved in EtOH (9 mL) and (5-methylisoxazol-3-yl)acetonitrile (0.65 g, 5.3 mmol) was added. The solution was stirred for 15 min then a solution of 2-azidobenzoic acid (0.7 g, 4.3 mmol) in EtOH (7 mL) was added and the mixture stirred for 1 h. After this time the mixture was heated at reflux for 5 h. The suspension was then allowed to cool to room temperature and the solvent removed in vacuo. The residue was taken up in water and 1N citric acid was added to pH4. The resultant precipitate was collected by filtration, washed with water then dried in vacuo at 60° C. The title compound (0.92 g, 80%) was isolated as a colourless solid. 1HNMR (360 MHz, d6-DMSO) δ 2.51 (3H, s), 6.83 (1H, q, J=0.8 Hz), 7.72 (1H, d of t, J=8.1 and 1.0 Hz), 8.01 (1H, d of t, J=7.5 and 1.4 Hz), 8.24 (1H, dd, J=8.0 and 1.3 Hz), 8.36 (1H, d, J=8.0 Hz), 12.16 (1H, br s).

Workup

  1. stirringthe mixture stirred for 1 h
  2. temperatureAfter this time the mixture was heated
  3. temperatureat reflux for 5 h
  4. customthe solvent removed in vacuo
  5. addition1N citric acid was added to pH4
  6. filtrationThe resultant precipitate was collected by filtration
  7. washwashed with water
  8. customthen dried in vacuo at 60° C

Sources & evidence

ORD record
ord-38a89390819547749b12c430ac170075
Source dataset
uspto-grants-2006_12
Patent number
US07144887B2

Reaction notes

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