Hydrochloric Acid → HCID 178446253, compound

HRID 1828949Notes

Reaction equation

HRID 1828949 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](O)=[CH:3][C:2]=1[OH:12].[CH2:13]([NH2:18])[C:14]([CH3:17])([CH3:16])[CH3:15].Cl.CN1C(=O)CCC1>C(O)(C)C>[CH3:15][C:14]([CH3:17])([CH3:16])[CH2:13][NH:18][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[C:2]([OH:12])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 79882NeopentylamineHCID 1785165532-hydroxy-1H-quinolin-4-one

Product 1

HCID 178446253HCID 178446253, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
180 °C

Procedure

2,4-Quinolinediol (15 g, 93 mmol), neopentyl amine (33 mL, 280 mmol), 6 N HCl in isopropanol (15 mL), and 40 mL NMP were place in a sealed tube and heated to 180° C. for 40 h. The reaction was then poured onto water (800 mL), stirred for 1 h and filtered. The cake was washed with water, collected and dried in vacuo (50 mTorrr, 60° C.) to afford 17.85 g (81.5%). 1H NMR (360 MHz, DMSO): 0.97 (s, 9H), 3.02(d, 2H, J=6.06 Hz), 5.41(s, 1H), 6.58(t, 1H, J=6.06 Hz), 7.08(t, 1H, J=7.67 Hz), 7.21(d, 1H, J=8.07 Hz), 7.43(dd, 1H, J=7.67, 7.27 Hz), 8.03(d, 1H, J=8.07 Hz), 10.73(s, 1H).

Workup

  1. additionThe reaction was then poured onto water (800 mL)
  2. filtrationfiltered
  3. washThe cake was washed with water
  4. customcollected
  5. customdried in vacuo (50 mTorrr, 60° C.)
  6. customto afford 17.85 g (81.5%)

Sources & evidence

ORD record
ord-3c5c3c869a2345bab898bb64f746829a
Source dataset
uspto-grants-2006_06
Patent number
US07060834B2

Reaction notes

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