Water → HCID 66664617, compound

HRID 2174939Notes

Reaction equation

HRID 2174939 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2Cl.[CH3:16][O:17][C:18]1[N:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1.O>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2[NH:24][C:21]1[CH:22]=[N:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 811216-Methoxy-3-pyridinylamineHCID 219841286-Bromo-4-chloro-3-nitroquinoline

Product 1

HCID 66664617HCID 66664617, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-Bromo-4-chloro-3-nitroquinoline (compound of step 1, 5.2 mmol) and 6-methoxypyridin-3-amine (commercially available, 5.2 mmol) was dissolved in acetic acid (5 mL) and the mixture was stirred overnight. Water was added and the yellow precipitate was filtered off. The precipitate was washed with water and dried. The solid obtained was partitioned and extracted with EtOAc and THF, washed with saturated aqueous NaHCO3. The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the title compound. 1H NMR (DMSO-d6, 300 MHz): 10.03 (s, 1H), 9.01 (s, 1H), 8.72 (d, J=1.5 Hz, 1H), 8.04-7.90 (m, 3H), 7.50 (dd, J=2.4, 8.7 Hz, 1H), 6.82 (d, J=9.0 Hz, 1H), 3.85 (s, 3H); MS (m/z): 377.0 (M+1)+.

Workup

  1. filtrationthe yellow precipitate was filtered off
  2. washThe precipitate was washed with water
  3. customdried
  4. customThe solid obtained
  5. customwas partitioned
  6. extractionextracted with EtOAc and THF
  7. washwashed with saturated aqueous NaHCO3
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9c08a981b1304f97a005d63f525aa1a5
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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