Acetic Acid → HCID 178518307, compound

HRID 1672468Notes

Reaction equation

HRID 1672468 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CC(O)=O.[O:16]([C:18]#[N:19])[Na].[OH-].[Na+]>O>[Br:11][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:2]=1[N:1]=[C:18]([OH:16])[N:19]=[C:4]2[OH:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 2702592-Amino-3-bromobenzoic acidHCID 178418852HCID 178418852, compound

Product 1

HCID 178518307HCID 178518307, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
35 °C

Procedure

To a 2000 mL flask charged with 2-amino-3-bromobenzoic acid (67.0 g, 310 mmol) was added water (750 mL) and AcOH (18.8 mL). The suspension was heated to 35° C. A solution of NaOCN (30.82 g, 403 mmol, 85% purity) in water (250 mL) was added dropwise at 35° C. The reaction mixture was stirred at 35° C. for 2 hrs. NaOH (415 g, 10.38 mol) was added in portions, the reaction temperature was kept below 40° C. during the addition. The mixture turned clear for a short time, then an off-white suspension was formed. The reaction mixture was cooled to room temperature, and filtered. The obtained solid was dissolved in hot water, pH was adjusted to 5 by addition of 6 N HCl. The resulting mixture was cooled to room temperature, and the precipitate was collected by filtration, rinsed with a small amount of DCM, cold MeOH, ether, then dried in vacuo to yield the title compound as a off-white solid (43.32 g, 58%). 1HNMR (DMSO-d6, 400 MHz): δ 11.60-11.40 (br s, 1H), 10.40-10.20 (br s, 1H), 7.92 (d, J=7.6 Hz, 1H), 7.90 (d, J=8.0 Hz, 1H), 7.12 (dd, J=7.6, 8.0 Hz, 1H).

Workup

  1. additionthe reaction temperature was kept below 40° C. during the addition
  2. customan off-white suspension was formed
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. dissolutionThe obtained solid was dissolved in hot water
  6. additionpH was adjusted to 5 by addition of 6 N HCl
  7. temperatureThe resulting mixture was cooled to room temperature
  8. filtrationthe precipitate was collected by filtration
  9. washrinsed with a small amount of DCM, cold MeOH, ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-b5de13861cfc4e7cb4393b35d5127d1c
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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