Succinic Acid → HCID 86630927, compound

HRID 2406419Notes

Reaction equation

HRID 2406419 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[C:5]2[C:10](=[C:11]([NH:13][CH2:14][CH2:15][CH2:16][NH2:17])[CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH3:18].[C:30]([OH:37])(=[O:36])[CH2:31][CH2:32][C:33]([OH:35])=[O:34]>CO>[CH3:1][O:2][C:3]1[C:4]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:27])[F:29])[CH:21]=2)=[C:5]2[C:10](=[C:11]([NH:13][CH2:14][CH2:15][CH2:16][NH2:17])[CH:12]=1)[N:9]=[C:8]([CH:31]([C:30]([OH:37])=[O:36])[CH2:32][C:33]([OH:35])=[O:34])[CH:7]=[C:6]2[CH3:18]

Participants

4

Reactant 2

HCID 1110Succinic AcidHCID 16048421HCID 16048421, compound

Product 1

HCID 86630927HCID 86630927, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the above phthalimide 10 in 100 mL of 65% hydrazine and 100 mL of ethanol was refluxed under argon for 3 hours. After cooling to room temperature, the solution was diluted with 10% aqueous KOH solution and extracted with dichloromethane three times. The combined extract was washed with brine, dried (K2CO3), concentrated, and column chromatographed on silica gel using dichloromethane and methanol as eluants to give 1.86 g (80% yield) of 6-methoxy-8-[(3-aminopropyl)amino]-4-methyl-5-(3-trifluoromethylphenyloxy)quinoline. 1H NMR (CDCl3) δ 8.40 (d, J=4 Hz, 1 H), 7.34 (t, J=8 Hz, 1 H), 7.21 (d, J=8 Hz, 1 H), 7.06 (m, 2 H), 6.93 (d, J=8 Hz, 1 H), 6.48 (s, 1 H), 6.4 (bs, 1 H, NH), 3.83 (s, 3 H, OMe), 3.42 (t, J=8 Hz, 2 H), 2.99 (t, J=8 Hz, 2 H), 2.62 (s, 3 H, Me), 1.98 (pentet, J=8 Hz, 2 H), 1.80 (bs, 2 H, NH2). 13C NMR (CDCl3) δ 160.0, 151.1, 145.0, 143.5, 142.7, 130.2, 125.2, 118.4, 118.2, 112.2, 107.5, 92.9, 56.8, 41.6, 40.4, 33.1, 23.4. The succinic acid salt was prepared by treating 0.457 g (1.12 mmol) of the quinoline with 0.134 g (1.13 mmol) of succinic acid in 10 mL of methanol. The resulting solution was concentrated to dryness, crystallized from diethyl ether to give a quantitative yield of the succinic acid salt PQ1.

Workup

  1. customThe succinic acid salt was prepared
  2. concentrationThe resulting solution was concentrated to dryness
  3. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-b4831eae8ebc4d528718dedd889c0e41
Source dataset
uspto-grants-2014_08
Patent number
US08809368B2

Reaction notes

Loading…