Water → HCID 86750368, compound

HRID 1451068Notes

Reaction equation

HRID 1451068 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].O.C([O-])(=O)C.[Na+].[N:17]#[C:18]Br>C(O)(=O)C>[OH2:6].[C:18]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 74193-Aminobenzoic AcidHCID 10476Cyanogen BromideHCID 517045Sodium Acetate

Product 1

HCID 86750368HCID 86750368, compoundYield 174.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 3-aminobenzoic acid (Aldrich, 9.05 g, 66 mmol) in acetic acid:water (70 mL, 1:1) was added sodium acetate (8.12 g, 99 mmol) and the mixture was cooled in an ice-water bath. Cyanogen bromide (8.38 g, 79.2 mmol) was added in two batches in 10 min and the stirring was continued for 18 h at room temperature. The reaction mixture was poured into 350 g of an ice-water mixture with stirring. The precipitate was collected through filtration, washed with cold water (about 70 mL), dried in air, and crystallized from methanol-water. The white solid was separated through filtration, dried in air followed by drying in a pistol at toluene reflux in vacuo to give 10.40 g (95%) of the title compound, mp 238°-240° C.

Workup

  1. temperaturethe mixture was cooled in an ice-water bath
  2. filtrationThe precipitate was collected through filtration
  3. washwashed with cold water (about 70 mL)
  4. customdried in air
  5. customcrystallized from methanol-water
  6. customThe white solid was separated through filtration
  7. customdried in air
  8. dry with materialby drying in a pistol at toluene
  9. temperaturereflux in vacuo

Sources & evidence

ORD record
ord-5162c8bb5d9f4ae083218fdee278cbb7
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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