Acetic Acid → HCID 178451560, compound

HRID 521419Notes

Reaction equation

HRID 521419 reaction equation
O=[C:2]1[C:11]2[CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][C:6]=2[NH:5][C:4]2[CH:19]=[CH:20][CH:21]=[C:22]([C:23]([O:25]C)=O)[C:3]1=2.O.[NH2:28][NH2:29].C(O)(=O)C.O>CC(N(C)C)=O.CCOC(C)=O>[O:25]=[C:23]1[C:22]2[C:3]3=[C:4]([CH:19]=[CH:20][CH:21]=2)[NH:5][C:6]2[CH2:7][N:8]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH2:9][CH2:10][C:11]=2[C:2]3=[N:29][NH:28]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 89657453HCID 89657453, compound

Product 1

HCID 178451560HCID 178451560, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

A solution of 2-tert-butyl 6-methyl 5-oxo-3,4,5,10-tetrahydrobenzo[b][1,7]naphthyridine-2,6(1H)-dicarboxylate (0.55 g) and hydrazine hydrate (2.5 mL) in DMA (4 mL) was heated at 130° C. for 2.0 h, acetic acid (4 mL) was added and the mixture was stirred at 130° C. for another 6 hours. The reaction mixture was cooled to room temperature, then water (30 mL) and EtOAc (100 mL) were added. The organic phase was separated and then washed with aqueous NaHCO3 (2×10 ml) and brine (20 ml), dried with Na2SO4 and filtered. The organic phase was concentrated in vacuum to give the crude product, which was then recrystallized from MeOH to afford the product (110 mg, 21%) as a yellow solid. 1H NMR (DMSO-d6) δ 11.7 (s, 1H), 10.52 (s, 1H), 7.60 (t, 1H, J=8.0 Hz), 7.43 (d, 1H, J=8.0 Hz), 7.21 (d, 1H, J=8.0 Hz), 4.22 (s, 2H), 3.54-3.55 (m, 2H), 2.30-2.33 (m, 2H), and 1.40 (s, 9H). MS (ESI) m/e [M+1]+341.0.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic phase was separated
  3. washwashed with aqueous NaHCO3 (2×10 ml) and brine (20 ml)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationThe organic phase was concentrated in vacuum
  7. customto give the crude product, which
  8. customwas then recrystallized from MeOH

Sources & evidence

ORD record
ord-f6f7ab787b8f4c43809d2bf7b4a2d090
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

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