Formic Acid → HCID 66987301, compound

HRID 555273Notes

Reaction equation

HRID 555273 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][OH:13])=[C:6]([NH2:14])[CH:5]=1.[CH:16](O)=O>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH2:11][CH2:12][OH:13])[CH:16]=[N:14][C:6]=2[CH:5]=1)=[O:15]

Participants

3

Reactant 2

HCID 284Formic Acid2×HCID 51358181HCID 51358181, compound

Product 1

HCID 66987301HCID 66987301, compoundYield 78%

Conditions

Temperature
45 °C

Procedure

3-Amino-4-(2-hydroxy-ethylamino)-benzoic acid methyl ester (2.6 g, 12.0 mmol) was dissolved in formic acid (20 mL). The solution was heated at 45° C. for 1 h. After checking the completion of reaction by TLC, formic acid was evaporated at <40° C. under reduced pressure and the resulting solid was recrystallized from EtOAc. The above solid was dissolved in 3N HCl, stirred at ambient temperature for 1 h, basified back with saturated sodium bicarbonate solution and extracted with EtOAc. The organic layer was evaporated to give 2.1 g (78%) of 1-(2-hydroxy-ethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester. MS-ESI m/z 221 (M+1): 1H NMR (300 MHz, DMSO-d6) δ 3.7 (q, 2H), 3.9 (s, 3H), 4.3 (t, 3H), 5.0 (t, 1H), 7.7 (d, 1H), 7.9 (dd, 1H), 8.25 (s, 1H), 8.35 (s, 1H)

Workup

  1. customwas evaporated at <40° C. under reduced pressure
  2. customthe resulting solid was recrystallized from EtOAc
  3. dissolutionThe above solid was dissolved in 3N HCl
  4. extractionextracted with EtOAc
  5. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-6344907218d44c418049a5ed578ea07f
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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