Ethanolamine → HCID 18945314, compound

HRID 399859Notes

Reaction equation

HRID 399859 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[NH2:18][CH2:19][CH2:20][OH:21].[BH4-].[Na+].C(=O)([O-])O.[Na+]>CO>[OH:21][CH2:20][CH2:19][NH:18][CH2:1][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 18945307Methyl 3-formyl-5-(1H-pyrrol-1-yl)benzoate

Product 1

HCID 18945314HCID 18945314, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-formyl-5-(pyrrol-1-yl)benzoate (1.66 g), 2-aminoethanol (0.88 ml) and molecular sieves 4A (1.7 g) in methanol (40 ml) was stirred for 6 hours at room temperature. Then, to the reaction mixture was added sodium borohydride (0.55 g). After stirring for 3 hours at room temperature, the reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution and filtered. The filtrate was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-(2-hydroxyethylaminomethyl)-5-(pyrrol-1-yl)benzoate (0.80 g).

Workup

  1. stirringAfter stirring for 3 hours at room temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo
  4. customthe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1)
  5. additionThe eluted fractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-cc8d283ec600441989534b614a89d54e
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

Loading…