Dimethylamine, hydrochloride → 4-(4-(Dimethylamino)-6-hydroxyquinolin-2-yl)benzoic acid

HRID 2280478Notes

Reaction equation

HRID 2280478 reaction equation
F[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH:3]=1.[NH:22]([CH3:24])[CH3:23].Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:23][N:22]([CH3:24])[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 56961213HCID 56961213, compound2×

Product 1

HCID 569593354-(4-(Dimethylamino)-6-hydroxyquinolin-2-yl)benzoic acidYield 32.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

30 mg of 4-(4-fluoro-6-hydroxyquinolin-2-yl)benzoic acid (Compound 26) was mixed with 1 mmol Me2NH.HCl and 0.5 ml DIEA in 3 ml DMF and heated to 160° C. for 30 minutes. The solvent was evaporated to dryness and water was added. The solid was filtered and washed with water and dried. The crude was triturated with acetone to obtain 10.5 mg of Compound 47. 1H NMR (DMSO-d6 300 MHz TMS): δ 13.2 (b, 1H), 10.28 (s, 1H), 8.22 (m, 2H), 8.11 (d, 1H), 7.99 (d, 1H), 7.50 (s, 1H), 7.39 (d, 1H), 7.26 (s, 1H), 3.24 (s, 6H), MS (ESI): m/z=309.30 [M+1]+.

Workup

  1. customThe solvent was evaporated to dryness and water
  2. additionwas added
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried
  6. customThe crude was triturated with acetone

Sources & evidence

ORD record
ord-b6f6f89350364352af37b66ca0bdaac6
Source dataset
uspto-grants-2015_09
Patent number
US09139528B2

Reaction notes

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