HCID 86629451, compound → HCID 86629452, compound

HRID 599295Notes

Reaction equation

HRID 599295 reaction equation
[C:1]([NH:5][C:6]1[CH:11]=[C:10]([Cl:12])[N:9]=[CH:8][C:7]=1[CH2:13][OH:14])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[C:1]([NH:5][C:6]1[C:7]([CH:13]=[O:14])=[CH:8][N:9]=[C:10]([Cl:12])[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86629451HCID 86629451, compound

Product 1

HCID 86629452HCID 86629452, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (4-tert-butylamino-6-chloro-pyridin-3-yl)-methanol (5.0 g, 23.4 mmol) and MnO2 (14.3 g, 163.6 mmol) in anhydrous CH2Cl2 (100 mL) was stirred at RT for 10 h. The reaction was filtered and the filtrate was concentrated to give 4-(tert-butylamino)-6-chloronicotinaldehyde (4.0 g, 87.0% yield), which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 9.83 (s, 1 H), 8.90 (s, 1 H), 8.44 (s, 1 H), 6.86 (s, 1 H), 1.40 (s, 9 H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7a114a0a1dda44599be9bd36e20d2440
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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