Ammonia → 2-Amino-3-methoxybenzamide

HRID 625770노트

반응식

HRID 625770 반응식
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CC[N:15](C(C)C)C(C)C.N.CO.CCN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1>CN(C=O)C.O>[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:15])=[O:5]

참가 물질

9

반응물 6

HCID 222AmmoniaHCID 887MethanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2557202-Amino-3-methoxybenzoic acid

생성물 1

HCID 185365712-Amino-3-methoxybenzamide수율 76%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To 2-amino-3-methoxybenzoic acid (8.11 g, 48.52 mmol) in DMF (150 mL) at rt were added DIEA (13.2 mL, 58.22 mmol), 2 N ammonia in MeOH (33.96 mL, 67.92 mmol), EDCI (11.16 g, 58.22 mmol), and 1-hydroxybenzotriazole (7.87 g, 58.22 mmol). The solution was stirred at rt under argon. After 20 h the solution was diluted with water and extracted ten times with EtOAc. The EtOAc volume was reduced and washed with brine. The EtOAc fraction was concentrated and diluted with diethyl ether. The resulting tan solid was collected and dried in vacuo to give 2-amino-3-methoxybenzamide (6.08 g, 76%). 1H NMR (300 MHz, DMSO-d6) δ 3.79 (s, 3H), 6.26 (bs, 2H), 6.48 (m, 1H), 6.88 (d, J=7.9 hz, 1H), 7.12 (bs, 1H), 7.19 (dd, J=8.2, 1.0 Hz, 1H), 7.70 (bs, 1H) LC-MS (ESI) m/z 167 (M+H)+.

후처리

  1. extractionextracted ten times with EtOAc
  2. washwashed with brine
  3. concentrationThe EtOAc fraction was concentrated
  4. additiondiluted with diethyl ether
  5. customThe resulting tan solid was collected
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-d416e5fda2cf4ba5a057f59ceb2503e0
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09308207B2

반응 노트

불러오는 중…