2-Fluoro-5-nitrobenzoic acid → HCID 178524576, compound

HRID 1934664Notes

Reaction equation

HRID 1934664 reaction equation
F[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]1>N1C=CC=CC=1>[OH:21][C@H:18]1[CH2:19][CH2:20][C@H:15]([NH:14][C:2]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 2809972-Fluoro-5-nitrobenzoic acidHCID 178511715HCID 178511715, compound

Product 1

HCID 178524576HCID 178524576, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-fluoro-5-nitrobenzoic acid (235 mg) in pyridine (1.5 mL) was added trans-4-aminocyclohexanol (292 mg), and the mixture was stirred for 3 hours at 80° C. After evaporation of the solvent, the residue was dissolved in water and neutralized with 1N-hydrochloric acid (1.9 mL). The resulting precipitates were collected by filtration and washed successively with water and methanol to give 2-(trans-4-hydroxycyclohexylamino)-5-nitrobenzoic acid (279 mg) as a solid substance.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in water and neutralized with 1N-hydrochloric acid (1.9 mL)
  3. customThe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed successively with water and methanol

Sources & evidence

ORD record
ord-a4621fcd072445059816d38235c04565
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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