Formic Acid → 1-Methyl-1H-benzimidazole-5-carboxylic acid

HRID 626241

반응식

HRID 626241 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][CH3:12])[C:5]([OH:7])=[O:6].[CH:13](O)=O>O>[CH3:12][N:11]1[C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[N:1]=[CH:13]1

참가 물질

4

반응물 2

HCID 284Formic AcidHCID 115211443-Amino-4-(methylamino)benzoic acid

생성물 1

HCID 49130631-Methyl-1H-benzimidazole-5-carboxylic acid수율 84%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
85 °C

실험 절차

To a stirred solution of 3-amino-4-(methylamino)benzoic acid (9 g, 1.0 eq) in 50 mL water, was added 50 mL formic acid and heated at 85° C. overnight. The mixture was cooled, concentrated in vacuo, and dissolved in water. Then 2N HCl was added to adjust pH to 1-3. The suspension was filtered and washed with water to give the product (9.7 g, 84%). 1H NMR (400 MHz, DMSO-d6) δ 9.48 (s, 1H), 8.37 (s, 1H), 8.12 (d, J=8.8 Hz, 1H), 8.00 (d, J=8.8 Hz, 1H), 4.06 (s, 3H).

후처리

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in water
  4. additionThen 2N HCl was added
  5. filtrationThe suspension was filtered
  6. washwashed with water

출처 및 근거

ORD 기록
ord-506f69e4209d47d4b3dc23f790744a31
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309211B2

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