3-Chloro-2-nitrobenzoic acid → HCID 11221793, compound

HRID 2298037Notes

Reaction equation

HRID 2298037 reaction equation
[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[C:20]12([CH2:30][NH2:31])[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2.C(N(CC)C(C)C)(C)C>ClCCl.CN(C)C=O.O>[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:31][CH2:30][C:20]12[CH2:29][CH:24]3[CH2:23][CH:22]([CH2:28][CH:26]([CH2:25]3)[CH2:27]1)[CH2:21]2)=[O:7]

Participants

8

Reactant 4

HCID 209023-Chloro-2-nitrobenzoic acidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamine

Product 1

HCID 11221793HCID 11221793, compoundYield 76.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 3-chloro-2-nitrobenzoic acid (2.68 g) in dichloromethane (10 ml) at 0° C. was added oxalyl chloride (3 ml) and dimethylformamide (1 drop). The resulting mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour, then concentrated under reduced pressure to yield a solid. The solid was dissolved in dichloromethane (10 ml) and cooled to 0° C. A solution of 1-adamantanemethylamine (2.19 g) and N,N-diisopropylethylamine (11 ml) in dichloromethane (10 ml) was added portion-wise and the resulting solution allowed to stir at room temperature under a nitrogen atmosphere for 2 h. The reaction mixture was poured into water and the organic phase separated and washed with 2N hydrochloric acid, 10% aqueous sodium hydroxide and saturated brine. The organic phase was then dried over sodium sulfate, filtered and concentrated under reduced pressure and the resulting solid recrystallized from iso-propanol to afford the subtitle compound as a solid (3.52 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto yield a solid
  3. temperaturecooled to 0° C
  4. stirringto stir at room temperature under a nitrogen atmosphere for 2 h
  5. customthe organic phase separated
  6. washwashed with 2N hydrochloric acid, 10% aqueous sodium hydroxide and saturated brine
  7. dry with materialThe organic phase was then dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customthe resulting solid recrystallized from iso-propanol

Sources & evidence

ORD record
ord-c366a7f8f99f441995f5fefc584397dd
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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