Hydrochloric Acid → 2-Carbamoyl-6-nitrobenzoic Acid

HRID 535782

반응식

HRID 535782 반응식
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:14])[NH:7][C:8]2=[O:13])([O-:3])=[O:2].[OH-:15].[Na+].Cl>O>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([C:8]([NH2:7])=[O:13])[C:5]=1[C:6]([OH:14])=[O:15])([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 117793-NitrophthalimideHCID 14798Sodium Hydroxide

생성물 1

HCID 45927482-Carbamoyl-6-nitrobenzoic Acid수율 96.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
2.5 °C

실험 절차

Commercially available 4-nitro-isoindole-1,3-dione (1) (25 g, 0.13 mol) was stirred in water (300 mL) at 0° C. Over a few minutes, an aqueous solution of sodium hydroxide (30% w/w, 35 g, 0.26 mol) was added. The mixture was stirred for 1.5 h at 0-5° C. The cold solution was acidified with concentrated HCl (22 mL, 0.26 mol) and the product precipitated as a white solid. After allowing to stand overnight in a refrigerator, the mixture was filtered to afford the title compound (26.3 g, 96%) as a white solid: 1H NMR (300 MHz, DMSO) δ 8.2 (s, 1H), 8.15 (d, 1H), 7.93 (d, 1H), 7.88-7.65 (m, 2H); ESIMS m/z 211 ([M+H]+), m/z 209 ([M−H]−).

후처리

  1. waitOver a few minutes
  2. customthe product precipitated as a white solid
  3. waitto stand overnight in a refrigerator
  4. filtrationthe mixture was filtered

출처 및 근거

ORD 기록
ord-a4e44332efb34e9ba8bf529f0a480742
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859558B2

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