Triethylamine → 10-[(2-Methylpropanoyl)oxy]-4-oxo-6,7-dihydro-4H-pyrimido[2,1-a]isoquinoline-3-carboxylic acid

HRID 1704827Notes

Reaction equation

HRID 1704827 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[OH:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][N:14]3[C:21](=[O:22])[C:20]([C:23]([OH:25])=[O:24])=[CH:19][N:18]=[C:15]32)=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][N:14]3[C:21](=[O:22])[C:20]([C:23]([OH:25])=[O:24])=[CH:19][N:18]=[C:15]32)=[CH:10][CH:9]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 22758848HCID 22758848, compound

Product 1

HCID 2275886310-[(2-Methylpropanoyl)oxy]-4-oxo-6,7-dihydro-4H-pyrimido[2,1-a]isoquinoline-3-carboxylic acidYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutyryl chloride (455 mg., 4.26 mmoles) was added to a stirred, cooled (ice-water) mixture of 6,7-dihydro-10-hydroxy-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylic acid (1.03 g., 3.87 mmoles) and triethylamine (785 mg., 7.75 mmoles) in methylene chloride (20 ml.). The mixture was concentrated to dryness and the residue was triturated with cold 1N HCl, and then crystallized from benzene to give the title compound 0.81 g. (64% yield). The product was recrystallized successively from ethyl acetate and methanol to give the analytical sample, m.p. 183°-185°.

Workup

  1. temperaturecooled
  2. concentrationThe mixture was concentrated to dryness
  3. customthe residue was triturated with cold 1N HCl
  4. customcrystallized from benzene

Sources & evidence

ORD record
ord-5feccf620b88479ba556e3f48bce9ab7
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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