2-Nitrophenol → HCID 66874125, compound

HRID 249902Notes

Reaction equation

HRID 249902 reaction equation
Cl[CH:2]1[NH:6][C:5]2=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[CH:9][C:10]([F:11])=[C:4]2[O:3]1.[N+:16](C1C=CC=CC=1O)([O-])=O.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[NH2:16][C:2]1[O:3][C:4]2[C:5](=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[CH:9][C:10]=2[F:11])[N:6]=1

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 66874783HCID 66874783, compound

Product 1

HCID 66874125HCID 66874125, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-chloro-7-fluoro-2,3-dihydrobenzoxazole-4-carboxylate (720 mg, 3.14 mmol), o-nitrophenol (660 mg, 4.71 mmol) and K2CO3 (0.96 g, 7.0 mmol), in THF (10 mL), was stirred at ambient for 2.5 h. The reaction mixture was filtered and gaseous ammonia was bubbled through the mother liquor for 10 min. The precipitate formed was filtered and washed with THF (20 mL). The combined THF fractions were concentrated, and the resulting residue crystallized from methanol to afford methyl 2-amino-7-fluorobenzoxazole-4-carboxylate (173 mg, 26%) as a pale yellow solid. 1H NMR and MS consistent.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customgaseous ammonia was bubbled through the mother liquor for 10 min
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. washwashed with THF (20 mL)
  6. concentrationThe combined THF fractions were concentrated
  7. customthe resulting residue crystallized from methanol

Sources & evidence

ORD record
ord-0a99e80b8b314c8f8ee912bb9a7480a9
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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