Hydrochloric Acid → HCID 58168100, compound

HRID 1029242Notes

Reaction equation

HRID 1029242 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27]C)=[O:26])=[CH:20][CH:19]=1.Cl.[Li+].[OH-]>CN1C(=O)CCC1.C1COCC1.O>[O:12]=[C:6]1[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[C:3]2[C:8](=[N:9][CH:10]=[CH:11][C:2]=2[NH:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:22][CH:23]=2)[NH:7]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 2761030Methyl 2-(4-aminophenyl)acetateHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 58168100HCID 58168100, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

83 (550 mg, 2.17 mmol), methyl 2-(4-aminophenyl)acetate (376 mg, 2.28 mmol), and HCl (0.65 mL, 2.17 mmol, 4.0 M in dioxane) were suspended in NMP (5 mL), and stirred for 3 h at 140° C. The reaction mixture was quenched with saturated aqueous NaHCO3 (100 mL), and stirred for 30 min. The resulting precipitate was filtered, washed with H2O, and dried under vacuum. The methyl ester intermediate (750 mg, 2.09 mmol) and LiOH (150 mg, 6.26 mmol) were dissolved in THF (4 mL) and H2O (4 mL), and stirred for 48 h at room temperature. The THF was removed, the mixture was diluted with H2O, and acidified to pH=5 with 1M HCl. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to provide 302 (550 mg, 76% yield) as a white solid. 1HNMR(DMSO-D6): 3.52(s, 2H), 6.97 (d, 1H), 7.13 (m, 2H), 7.21 (m, 2H), 7.58 (m, 1H), 7.61 (m, 1H)m 8.10 (d, 1H), 8.34(d, 1H), 8.84-8.90 (m, 2H). LC-MS (M+H=346, obsd.=346).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NaHCO3 (100 mL)
  2. stirringstirred for 30 min
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with H2O
  5. customdried under vacuum
  6. customThe THF was removed
  7. additionthe mixture was diluted with H2O
  8. filtrationThe resulting precipitate was filtered
  9. washwashed with H2O
  10. customdried under vacuum

Sources & evidence

ORD record
ord-ac5d762cc7d84b2ba91ccf5c183e9223
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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