Sodium Hydroxide → HCID 811100, compound

HRID 1887434Notes

Reaction equation

HRID 1887434 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[C:5]([NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:11]=[C:10]([N+:21]([O-])=O)[CH:9]=1)=[O:6].[OH-].[Na+]>Cl.CO.[Zn]>[NH2:21][C:10]1[CH:9]=[C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:24]=[CH:25][CH:26]=[C:2]([Cl:1])[CH:3]=2)[CH:13]=[C:12]([O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:11]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 1040007HCID 1040007, compound

Product 1

HCID 811100HCID 811100, compoundYield 85.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Compound 1 (710 mg, 1.92 mmol, 1.00 eq) was dissolved in 1N HCl in MeOH (22 mL) and zinc (377 mg, 5.77 mmol, 3.00 eq) was added. The reaction was stirred for 1 hour and additional zinc (251 mg, 3.84 mmol, 2.00 eq) was added to drive the reaction to completion as determined by TLC. The reaction was neutralized with 1N NaOH, filtered and extracted with CH2Cl2 (3×). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 555 mg (85%) of the title compound as a brown solid: 1H NMR (400 MHz, DMSO-d6) δ 10.09 (s, 1H), 8.37 (dd, J=2.7, 0.8 Hz, 1H), 8.34 (dd, J=4.3, 1.7 Hz, 1H), 7.93 (t, J=1.8 Hz, 1H), 7.84 (dt, J=7.9, 1.2 Hz, 1H), 7.63 (ddd, J=8.1, 2.1, 1.0 1H), 7.52 (t, J=7.8 Hz, 1H), 7.43 (m, 2H), 6.94 (t, J=1.8 Hz, 1H), 6.62 (t, J=2.0 Hz, 1H), 6.00 (t, J=2.1 Hz, 1H), 5.37 (s, 2H); ES-MS [M+1]+: 340.1.

Workup

  1. customthe reaction to completion
  2. filtrationfiltered
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-714f0e1054be47ccb1d8d583e641295f
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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