Sodium Hydroxide → HCID 20200705, compound

HRID 2258410Notes

Reaction equation

HRID 2258410 reaction equation
Cl[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[OH-:12].[Na+].Cl.[NH2:15][OH:16]>O>[C:7]([C:6]1[CH:10]=[CH:11][C:3]([CH2:2][N:15]([CH2:2][C:3]2[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=2)[OH:16])=[CH:4][CH:5]=1)([OH:8])=[O:12]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide3×HCID 742344-(Chloromethyl)benzoic acidHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 20200705HCID 20200705, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A filtered solution of 4-(chloromethyl)benzoic acid (33.0 g, 186 mmol) and NaOH (7.43 g, 186 mmol) was added over a 5 minute period to a solution of hydroxylamine hydrochloride (6.45 g, 92.8 mmol), NaOH (3.7 g, 92.8 mmol) and water (100 mL). The solution was stirred mechanically, and heated to 45° C. The pH of the solution was kept at 8-10 by the addition of aqueous NaOH. When the pH of the solution stopped decreasing, the solution was filtered, then acidified with concentrated H2SO4 to a pH of 4. The resulting white solid was isolated by filtration and washed with copious amounts of water until no cloudiness was observed when the filtrate was treated with aqueous silver nitrate. The product was dried in vacuo then dissolved in boiling N,N-dimethylformamide (DMF) (60 mL) and the hot solution treated with water until slightly turbid. The solution was cooled and the white solid which formed was isolated by filtration, washed with water, and dried in vacuo at 70° C. at 0.01 Torr to give 10.9 g (39%) product. The product met the following criteria: 1H NMR (DMSO-d6) δ 12.87 (br, s, 2H), 7.86 (d, J=7.5 Hz, 4H), 7.45 (d, J=7.5 Hz, 4H), 3.87 (s, 4H). 13C {1H} NMR (DMSO-d6) δ 167.3, 143.6, 129.4, 129.1, 129.0, 63.5. Analyzed for C16H15NO5 : C, 63.78; H, 5.02; N, 4.65. Found: C, 63.62; H, 5.11; N, 4.84.

Workup

  1. filtrationthe solution was filtered
  2. customThe resulting white solid was isolated by filtration
  3. washwashed with copious amounts of water until no cloudiness
  4. additionwas treated with aqueous silver nitrate
  5. customThe product was dried in vacuo
  6. dissolutionthen dissolved
  7. additionthe hot solution treated with water until slightly turbid
  8. temperatureThe solution was cooled
  9. customthe white solid which formed
  10. customwas isolated by filtration
  11. washwashed with water
  12. customdried in vacuo at 70° C. at 0.01 Torr

Sources & evidence

ORD record
ord-84c8b0268c7348aea6860932ac9579a8
Source dataset
uspto-grants-1997_08
Patent number
US05660974

Reaction notes

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