Hydrochloric Acid → HCID 90411044, compound

HRID 717349Notes

Reaction equation

HRID 717349 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][C:14]1[N:23]=[C:22]([C:24]([O:26]CC)=[O:25])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.[OH-].[K+].Cl>O>[NH2:3][CH2:12][CH2:13][C:14]1[N:23]=[C:22]([C:24]([OH:26])=[O:25])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 90411447HCID 90411447, compound

Product 1

HCID 90411044HCID 90411044, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Into a 250-mL 4-necked round-bottom flask, was placed ethyl 2-[2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)ethyl]quinazoline-4-carboxylate (7 g, 18.65 mmol, 1.00 equiv). This was followed by the addition of KOH (20.9 g, 372.51 mmol, 19.98 equiv) in water (20 mL) dropwise with stirring. The resulting solution was stirred for 18 h at 100° C. The reaction was then poured into 250 mL of water. The pH value of the solution was adjusted to 7 with hydrogen chloride (2 mol/L). The resulting solution was extracted with 5×100 mL of ethyl acetate and the organic layers combined. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 3.2 g (79%) of 2-(2-aminoethyl)quinazoline-4-carboxylic acid as a white solid. MS (ESI) m/z 218 ([M+H]+).

Workup

  1. customInto a 250-mL 4-necked round-bottom flask, was placed
  2. stirringThe resulting solution was stirred for 18 h at 100° C
  3. extractionThe resulting solution was extracted with 5×100 mL of ethyl acetate
  4. dry with materialThe mixture was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 3.2 g (79%) of 2-(2-aminoethyl)quinazoline-4-carboxylic acid as a white solid

Sources & evidence

ORD record
ord-8df241b43a774e15827ec1723e742f5a
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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