Ethanolamine → HCID 4319814, compound

HRID 2384523Notes

Reaction equation

HRID 2384523 reaction equation
[C:1]([OH:13])(=O)[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C[N:15]1CC[O:18][CH2:17][CH2:16]1.C(OC(Cl)=O)C(C)C.C(CN)O>C(Cl)Cl>[OH:18][CH2:17][CH2:16][NH:15][C:1]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)=[O:13]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 7124Quinaldic AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformate

Product 1

HCID 4319814HCID 4319814, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an oven dried 250 mL round bottomed flask was weighed quinaldic acid (1.734 g, 10.0 mmol). A magnetic stir bar was added and the flask was put under N2 atmosphere. The flask was charged with DCM (100 mL) and cooled to 0° C. in an ice bath. The flask was then charged with N-methyl morpholine (1.44 mL, 15.0 mmol) and isobutlychloroformate (1.51 mL, 11.5 mmol) via syringe addition. The reaction was allowed to stir at 0° C. for 20 min until the solution became cloudy. At which point freshly distilled ethanolamine (695 uL, 11.5 mmol) was added slowly to the flask via syringe. The reaction mixture was allowed to slowly warm to room temperature to form N-(2-hydroxyethyl)quinoline-2-carboxamide was formed according to the formula

Workup

  1. customTo an oven dried 250 mL round bottomed flask
  2. additionA magnetic stir bar was added
  3. additionaddition
  4. temperatureto slowly warm to room temperature

Sources & evidence

ORD record
ord-d65367be521042cb9b0b807276c48ed6
Source dataset
uspto-grants-2012_09
Patent number
US08263774B2

Reaction notes

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