Hydrochloric Acid → HCID 53981819, compound

HRID 1755931Notes

Reaction equation

HRID 1755931 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[O:5])[CH3:2].[NH2:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.Cl>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 111584-AminobenzaldehydeHCID 3045573-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl ester

Product 1

HCID 53981819HCID 53981819, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

4-Chloro-8-methoxy-3-quinolinecarboxylic acid ethyl ester (10.62 g, 40 mmol) and 4-aminobenzaldehyde (4.85 g, 40 mmol) were suspended in dry DMF (100 mL) and treated dropwise with concentrated HCl (aq) (3.3. mL, 40 mmol). The mixture was heated at 90° C. for 40 min. After dilution with methylene chloride (800 mL) the reaction mixture was extracted with 1N NaOH (200 mL) and water (3×200 mL) and the dried (MgSO4) organic phase evaporated to a yellow oil. Crystallization from a minimum amount of ether afforded 8.0 g (22.8 mmol), 57% yield) of the product as a light yellow solid: m.p. 108°-110° C. (dec): 1H NMR (Me2SO-d6, 400 MHz) δ 9.79 (s, 1 H), 9.70 (s, 1 H), 8.99 (s, 1 H), 7.75 (d, J=8.7 Hz, 2 H), 7.64 (d, J=7.9 Hz, 1 H), 7.52 (t, J=7.9 Hz, 1 H), 7.31 (d, J=7.9 Hz, 1 H), 7.01 (d, J=8.5 Hz, 2 H), 4.02 (q, J=7.1 Hz, 2 H), 3.99 (s, 3 H), 1.08 (t,J=7.1 Hz, 3 H); MS(EI), m/z (rel. intensity)=350 (M+, 100), 321(34), 275(68), 247(58), 218(35), 205(18), 190(21); IR(KBr) 3430, 3350, 2820, 2740, 1685, 1590, 1500, 1390, 1270, 1215, 1160, 1060, 1020, 770cm-1.

Workup

  1. extractionAfter dilution with methylene chloride (800 mL) the reaction mixture was extracted with 1N NaOH (200 mL) and water (3×200 mL)
  2. dry with materialthe dried (MgSO4) organic phase
  3. customevaporated to a yellow oil
  4. customCrystallization from a minimum amount of ether

Sources & evidence

ORD record
ord-ce04d8a7b44f4b52a39c4189576a578f
Source dataset
uspto-grants-1995_08
Patent number
US05438064

Reaction notes

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