Phenol → HCID 19900493, compound

HRID 1029436Notes

Reaction equation

HRID 1029436 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:14]([O:16]C)=[O:15])[CH:3]=1.[CH3:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH2:22].C1(O)C=CC=CC=1>C(OCC)(=O)C>[CH3:13][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([C:14]([OH:16])=[O:15])[CH:3]=[C:2]2[NH:22][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=1[CH3:18]

Participants

5

Reactant 3

HCID 996PhenolHCID 69932-MethylbenzylamineHCID 9878216HCID 9878216, compound

Product 1

HCID 19900493HCID 19900493, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 54 g (=215 mmol) of methyl 4-chloro-8-methoxyquinoline-2-carboxylate, 33.7 g (=278 mmol) of 2-methylbenzylamine and 243 g (=2.58 mmol) of phenol was heated at 140° C. in an autoclave for 4 hours. The cooled reaction mixture was added dropwise to 4 1 of ethyl acetate, and the resulting precipitate was filtered off with suction. The solid was dissolved in 1 1 of THF and the pH was adjusted to 10 with 10% NaOH. The mixture was stirred at 50° C. for 1 hour, maintaining the pH constant, cooled to 10° C. and adjusted to pH 5-6 with dilute HCl. This resulted in the product crystallizing. 18.85 g of 8-methoxy-4-(2-methylbenzylamino)quinoline-2-carboxylic acid of melting point 276-277° C. were obtained.

Workup

  1. customThe cooled reaction mixture
  2. filtrationthe resulting precipitate was filtered off with suction
  3. dissolutionThe solid was dissolved in 1 1 of THF
  4. temperaturemaintaining the pH constant,
  5. temperaturecooled to 10° C.
  6. customThis resulted in the product
  7. customcrystallizing

Sources & evidence

ORD record
ord-f17aa74c957d4a03ae6d739a14e5a5c7
Source dataset
uspto-grants-1992_04
Patent number
US05102892

Reaction notes

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