Sodium Carbonate → HCID 3348523, compound

HRID 874922Notes

Reaction equation

HRID 874922 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])#[N:2].Cl.[NH2:13][OH:14].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.OC1C=CC=C2C=1N=CC=C2>[OH:14][N:13]=[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])[NH2:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 158753-Cyanobenzoic acidHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3348523HCID 3348523, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 19238-HydroxyquinolineCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

8-Hydroxyquinoline (5 mg, 0.03 mmol) was added to a solution of 3-cyanobenzoic acid (1 g, 6.8 mmol) in 50 mL ethanol. To this reaction mixture were added first hydroxylamine hydrochloric acid (950 mg, 13.6 mmol) in water (8 mL) followed by sodium carbonate (1.2 g, 10.9 mmol) in water (12 mL). The mixture was heated to reflux for 4 h. After removal of ethanol under reduced pressure, the residue was diluted with water, and the aqueous solution was acidified with 10% HCl to pH˜3. The white precipitate was filtrated, washed with water and acetone and then dried under reduced pressure to afford compound 3-(N′-hydroxycarbamimidoyl)benzoic acid (1 g, yield 82%): 1H NMR (400 MHz, CDCl3) δ 13.03 (br s, 1H), 9.76 (s, 1H), 8.27-8.26 (m, 1H), 7.95-7.89 (m, 2H), 7.53 (t, J=7.8 Hz, 1H), 5.94 (br s, 2H). MS (ESI) m/z: Calculated for C8H8N2O3: 180.05. found: 180.9 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. customAfter removal of ethanol under reduced pressure
  4. additionthe residue was diluted with water
  5. filtrationThe white precipitate was filtrated
  6. washwashed with water and acetone
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-4a7632db97af44c88c918edb4dcf3275
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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