(5-Aminobenzo[f][1,7]naphthyridin-8-yl)methanol → 5-Aminobenzo[f][1,7]naphthyridine-8-carbaldehyde

HRID 1259169Notes

Reaction equation

HRID 1259169 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]=[CH:13][C:14]([CH2:16][OH:17])=[CH:15][C:4]=2[N:3]=1>C(Cl)Cl.O=[Mn]=O>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[CH:13][C:14]([CH:16]=[O:17])=[CH:15][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 44232402(5-Aminobenzo[f][1,7]naphthyridin-8-yl)methanol

Product 1

HCID 866523555-Aminobenzo[f][1,7]naphthyridine-8-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (5-aminobenzo[f][1,7]naphthyridin-8-yl)methanol (from Example 85) (1.0 eq.) and activated MnO2 (20 eq.) in DCM (0.1 M) was stirred at ambient temperature over night. The reaction mixture was diluted with DCM. The MnO2 was filtered off, and the filtrate was concentrated en vaccuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% MeOH/DCM to give 5-aminobenzo[f][1,7]naphthyridine-8-carbaldehyde as a yellow solid: 1H NMR (acetone-d6): δ 10.19 (s, 1H), 9.14 (dd, 1H), 9.01 (dd, 1H), 8.63 (d, 1H), 8.14 (d, 1H), 7.93 (dd, 1H), 7.81 (dd, 1H), 6.96 (br s, 2H). LRMS [M+H]=224.1

Workup

  1. filtrationThe MnO2 was filtered off
  2. concentrationthe filtrate was concentrated en vaccuo
  3. customto obtain a crude residue
  4. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-d377f0ff52bd472fa21657818aa2a2e2
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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