Methyl 6-amino-4-(chroman-6-yl)-5-(hydroxymethyl)-2-methylnicotinate → Methyl 6-amino-4-(chroman-6-yl)-5-formyl-2-methylnicotinate

HRID 1912544Notes

Reaction equation

HRID 1912544 reaction equation
[NH2:1][C:2]1[C:11]([CH2:12][OH:13])=[C:10]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[O:20][CH2:19][CH2:18][CH2:17]3)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:24])[N:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[NH2:1][C:2]1[C:11]([CH:12]=[O:13])=[C:10]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[O:20][CH2:19][CH2:18][CH2:17]3)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:24])[N:3]=1

Participants

4

Reactant 2

HCID 71209315Methyl 6-amino-4-(chroman-6-yl)-5-(hydroxymethyl)-2-methylnicotinateHCID 178418287HCID 178418287, compound

Product 1

HCID 86675740Methyl 6-amino-4-(chroman-6-yl)-5-formyl-2-methylnicotinateYield 66.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of crude methyl 6-amino-4-(chroman-6-yl)-5-(hydroxymethyl)-2-methylnicotinate in dichloromethane (DCM) (264 mL) was treated with PCC (5.78 g, 26.8 mmol) and the mixture was stirred overnight at ambient temperature. The mixture was filtered over Celite™ and the filtrate was concentrated and purified on silica gel to afford methyl 6-amino-4-(chroman-6-yl)-5-formyl-2-methylnicotinate as a yellow solid (4.5 g, 13.79 mmol, 66.8% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.66 (s, 1 H), 7.00 (dd, J=2.0, 8.3 Hz, 1 H), 6.95 (s, 1 H), 6.84 (d, J=8.4 Hz, 1 H), 4.26-4.23 (m, 2 H), 3.54 (s, 3 H), 2.81 (t, J=6.4 Hz, 2 H), 2.48 (s, 3 H), 2.08-2.02 (m, 2 H); LC/MS (m/z) ES+=327.25 (M+1).

Workup

  1. filtrationThe mixture was filtered over Celite™
  2. concentrationthe filtrate was concentrated
  3. custompurified on silica gel

Sources & evidence

ORD record
ord-ef31178866f74a799052e9d66305f2c1
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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