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Acetyl chloride → HCID 22006271, compound

HRID 323650
Notes
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Reaction equation

HRID 323650 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)[N:13]=[C:12]([OH:24])[C:8]=3[NH:9][C:10]=2[CH:11]=1.[C:25](Cl)(=[O:27])[CH3:26].N1C(C)=CC=CC=1C>C1(C)C=CC=CC=1.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)[N:13]=[C:12]([O:24][C:25](=[O:27])[CH3:26])[C:8]=3[NH:9][C:10]=2[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 79372,6-LutidineHCID 178426276HCID 178426276, compound

Product 1

HCID 22006271HCID 22006271, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283
Diethyl Ether
Solvent

Procedure

A suspension of the 7-chloro-4-hydroxy-2-(4′-methylphenyl)-5,10-dihydro-2H-pyridazino[4,5-b]quinoline-1-one (755 mg), acetyl chloride (0.205 mL) and 2,6-lutidine (0.337 mL) was refluxed in toluene (6 mL) for 2 hours. The resulting mixture was cooled to room temperature. The resulting paste was diluted with ether (15 mL) and filtered in vacuo. The solids were washed with ether and ethyl acetate. The crude solids were triturated in warm ethyl acetate, then cooled to room temperature and filtered in vacuo. After drying this afforded the title compound as a light yellow solid (528 mg, 62%). mp 238-240° C.; MS 382 (m+H); NMR 2.34(s,3H), 2.41(s,3H), 3.85(s, 2H), 6.98(dd,1H,J1=8.1,J2=1.9), 7.09(d,1H,J=1.9), 7.18(d,1H,J=8.1), 7.28(d,2H,J=8.3), 7.39(d,2H,J=8.3), 9.06(s,1H); Analysis C20H16ClN3O3. 0.03M H2O expected/theoretical C 62.09/62.04H 4.24/2.27 N 10.62/10.85.

Workup

  1. filtrationfiltered in vacuo
  2. washThe solids were washed with ether and ethyl acetate
  3. customThe crude solids were triturated in warm ethyl acetate
  4. temperaturecooled to room temperature
  5. filtrationfiltered in vacuo
  6. customAfter drying

Sources & evidence

ORD record
ord-93e156d51cc24d58afe5e7eaa4073c99
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06214826B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes