Sodium Bicarbonate → 1-[(cyclopropylmethyl)amino]-4-hydroxyquinolin-2(1H)-one

HRID 601340Notes

Reaction equation

HRID 601340 reaction equation
[NH2:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]1=[O:13].[CH2:14]1[CH:16]([CH:17](O)C#N)[CH2:15]1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.[Cl-].[Na+].O.C(O)(=O)C>[CH:16]1([CH2:17][NH:1][N:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([OH:12])=[CH:4][C:3]2=[O:13])[CH2:14][CH2:15]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 113893592-Cyclopropyl-2-hydroxyacetonitrileHCID 591688071-amino-4-hydroxyquinolin-2(1H)-one

Product 1

HCID 670640181-[(cyclopropylmethyl)amino]-4-hydroxyquinolin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To the suspension of the product of Example 350A (1.033 g, 5.86 mmol) in methanol (58 mL) was added acetic acid (0.29 mL) and cyclopropylcarboxaldehyde (482 μL, 6.45 mmol) followed by the addition of sodium cyanoborohydride (744.6 mg, 11.85 mmol) at room temperature. The suspension was stirred at room temperature overnight and quenched with half saturated brine (100 mL) and sodium bicarbonate (425 mg, 5.06 mmol). The mixture was extracted with ethyl acetate (300 mL) and the organic layer was separated and washed with half saturated brine (2×50 mL). The combined aqueous layers were extracted with dichloromethane (2×100 mL). The combined organic solution was dried with magnesium sulfate, filtered and concentrated. The residue was used without any purification. 1H NMR (300 MHz, DMSO-d6) δ 0.09 (m, 2 H) 0.40 (m, 2 H) 0.95 (m, 1 H) 2.70 (t, J=6.43 Hz, 2 H) 5.91 (s, 1 H) 6.10 (t, J=6.07 Hz, 1 H) 7.21 (m, 1 H) 7.62 (t, J=7.17 Hz, 1 H) 7.87 (m, 2 H) 11.42 (br s, 1 H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (300 mL)
  2. customthe organic layer was separated
  3. washwashed with half saturated brine (2×50 mL)
  4. extractionThe combined aqueous layers were extracted with dichloromethane (2×100 mL)
  5. dry with materialThe combined organic solution was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was used without any purification

Sources & evidence

ORD record
ord-fb5cfca7bf8644948496e01347546113
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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