Pyridine → HCID 18472005, compound

HRID 2227135Notes

Reaction equation

HRID 2227135 reaction equation
[F:1][C:2]1[CH:3]=[C:4](N)[C:5](=[CH:10][C:11]=1[F:12])[C:6]([O:8][CH3:9])=[O:7].ClC(O[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=O.[N:27]1[CH:32]=CC=CC=1.C1C[O:36]CC1>C(#N)C>[N+:24]([C:21]1[CH:20]=[CH:19][C:18]([NH:27][C:32]([C:4]2[CH:3]=[C:2]([F:1])[C:11]([F:12])=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])=[O:36])=[CH:23][CH:22]=1)([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 821294-Nitrophenyl chloroformateHCID 18472001Methyl 2-amino-4,5-difluorobenzoate

Product 1

HCID 18472005HCID 18472005, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 4,5-difluoroanthranilate (0.19 g, 1 mmol) in THF (1.5 ml) was added at ca. 0° C. to p-nitrophenyl chloroformate (0.21 g, 1.05 mmol) in pyridine (0.089 ml, 1.1 mmol) and dry acetonitrile (2.0 ml). The mixture was stirred at r.t. for 2 h. Solvent was removed in vacuo, and the residue triturated with ethyl ether (ca. 3 ml), filtered, washed with ether (2×2 ml), water (3×3 ml), hexanes (3×5 ml), and dried in vacuo. Yield 0.27 g (77%). 1H NMR in CDCl3 (δ,ppm): 3.98 (s, 3 H), 7.40 (d, J=8.1 Hz, 2 H), 7.90 (m, 1 H), 8.30 (d, J 8.1 Hz, 2 H), 8.38 (m, 1 H), 11.07 (s, 1 H).

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue triturated with ethyl ether (ca. 3 ml)
  3. filtrationfiltered
  4. washwashed with ether (2×2 ml), water (3×3 ml), hexanes (3×5 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-78c5a22c696548a3810951c35e244774
Source dataset
uspto-grants-2002_07
Patent number
US06413724B1

Reaction notes

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