Water → Isophthalamic acid

HRID 393051노트

반응식

HRID 393051 반응식
IC1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](N)=[O:6].[OH2:11].C([N:14]([CH2:17][CH3:18])CC)C.C1(P(C(P(C2C=CC=CC=2)C2C=CC=CC=2)(C)C)C2C=CC=CC=2)C=CC=CC=1.[C]=[O:49]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:5]([C:4]1[CH:3]=[C:18]([CH:10]=[CH:9][CH:8]=1)[C:17]([NH2:14])=[O:49])([OH:11])=[O:6]

참가 물질

8

반응물 5

HCID 962WaterHCID 8471TriethylamineHCID 2024253-IodobenzamideHCID 12091099Phosphine, (1-methylethylidene)bis[diphenyl-HCID 178418416HCID 178418416, 화합물

생성물 1

HCID 3014284Isophthalamic acid수율 87%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

반응 조건

온도
85 °C

실험 절차

A mixture of 3-iodobenzamide (4.28 g, 17.3 mmol), water (25.00 g, 1387.7 mmol), triethylamine (8.00 g, 79.1 mmol), palladium(II) acetate (0.28 g, 1.2 mmol), and bis(diphenylphosphino)propane (0.52 g, 1.3 mmol) in acetonitrile (50 mL) was pressurized to 40 psi with carbon monoxide and the pressure was released. After six such cycles, the bottle was pressurized again and the contents were stirred at 85° C. for 3 h. The reaction mixture was cooled to room temperature and depressurized. The solvent was evaporated and ethyl acetate (200 mL) was added. The solution was filtered and then extracted with water (2×200 mL). The combined aqueous layers were acidified with 12 M HCl to pH 0. The solid was filtered off and air-dried to give 3-carboxybenzamide (1.93 g, 87%) as a yellow solid

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solvent was evaporated
  3. additionethyl acetate (200 mL) was added
  4. filtrationThe solution was filtered
  5. extractionextracted with water (2×200 mL)
  6. filtrationThe solid was filtered off
  7. customair-dried

출처 및 근거

ORD 기록
ord-c16d97f77c774ac9baa2d1dd38d7de1a
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06803384B2

반응 노트

불러오는 중…