Sodium Hydroxide → HCID 58213514, compound

HRID 340189Notes

Reaction equation

HRID 340189 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[C:13]([C:16]([O:18]CC)=[O:17])[CH:14]=[CH:15][C:4]=2[N:3]=1.[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=[CH:15][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44230475HCID 44230475, compound

Product 1

HCID 58213514HCID 58213514, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 5-aminobenzo[f][1,7]naphthyridine-9-carboxylate (Example 8) (1.0 eq.) was mixed with 1N NaOH (2.0 eq.) in ethanol (0.12 M). The reaction was heated to 80° C. and stirred for 36 hours. The solvent was removed en vacuo. The residue was suspended in water, and the pH was adjusted to neutral using 5% citric acid aqueous solution. The suspension was centrifuged (2500 rpm, 5 min), and the supernatant was removed. The resulting solids was re-suspended in water by vortexing, centrifuged (2500 rpm, 5 min), and the supernatant was removed. The re-suspension, centrifugation, and removal of supernatant steps were repeated with hot methanol, hot ethyl acetate, and ether to give a pure solid. 1H NMR (DMSO): δ 12.86 (s, 1H), 9.15 (d, 1H), 9.00 (s, 1H), 8.97 (d, 1H), 8.07 (d, 1H), 7.88-7.91 (dd, 1H), 7.56-7.59 (m, 3H). LRMS [M+H]=240.1

Workup

  1. customThe solvent was removed en vacuo
  2. custom(2500 rpm, 5 min)
  3. customthe supernatant was removed
  4. custom(2500 rpm, 5 min)
  5. customthe supernatant was removed
  6. customThe re-suspension, centrifugation, and removal of supernatant steps
  7. customto give a pure solid

Sources & evidence

ORD record
ord-5c28eb485174435e90ee5f8838618bc9
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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