4-Hydroxymethyl-3-nitrobenzoic acid → 4-Carboxy-2-nitrobenzyl isonicotinate

HRID 491242

반응식

HRID 491242 반응식
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].Cl.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[C:16]([O:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13])(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1

참가 물질

4

반응물 2

HCID 15018924-Hydroxymethyl-3-nitrobenzoic acidHCID 12262826Isonicotinoyl chloride hydrochloride

생성물 1

HCID 576769254-Carboxy-2-nitrobenzyl isonicotinate

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

4-[N-(3-triethoxysilyl)propyl]-carbamoyl-2-nitrobenzyl isonicotinate (TCNI) which binds to silicon dioxide through the ethoxysilyl groups, and has a pyridine metal binding group and a nitrobenzyl radiation sensitive group was prepared according to the synthetic procedure represented in Scheme 2. 4-Bromomethyl-3-nitrobenzoic acid (A) was refluxed overnight with sodium carbonate in acetone/water (1:1). After cooling to room temperature, the reaction mixture was made acidic with 1 N hydrochloric acid and the product was extracted into ethyl acetate, dried over magnesium sulfate and rotary evaporated to yield 4-hydroxymethyl-3-nitrobenzoic acid. The 4-hydroxymethyl-3-nitrobenzoic acid (B) was dissolved in pyridine and reacted with isonicotinoyl chloride hydrochloride at room temperature for 2 days. The resultant solution was poured onto ice, stirred overnight at room temperature and extracted with ethyl acetate. The organics were dried over magnesium sulfate and rotary evaporated to remove the solvents. Residual pyridine was removed by the addition of toluene followed by rotary evaporation. The resultant solid was slurried in ethanol at room temperature and the product, 4-carboxy-2-nitrobenzyl isonicotinate, was isolated by filtration and dried under vacuum.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organics were dried over magnesium sulfate
  3. customrotary evaporated
  4. customto remove the solvents
  5. customResidual pyridine was removed by the addition of toluene
  6. customfollowed by rotary evaporation
  7. customwas slurried in ethanol at room temperature

출처 및 근거

ORD 기록
ord-30e2ae30c10e4527b6fc19e59f750582
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531293B2

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