6-Amino-o-cresol → HCID 10688507, compound

HRID 1597059Notes

Reaction equation

HRID 1597059 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH3:9])[C:7]=1[OH:8].[CH2:10]([O:17][C:18]([NH:20][C@@H:21]([CH3:33])[CH:22]([C:24]1OC2C=CC=CC=2N=1)[OH:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCOC(C)=O>[CH2:10]([O:17][C:18]([NH:20][C@@H:21]([CH3:33])[CH:22]([C:24]1[O:8][C:7]2[C:6]([CH3:9])=[CH:5][CH:4]=[CH:3][C:2]=2[N:1]=1)[OH:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 4136576-Amino-o-cresolHCID 10711225HCID 10711225, compound

Product 1

HCID 10688507HCID 10688507, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This material was prepared as a 1:1 mixture of isomers in 57% yield from the above cyanohydrin (609 mg, 2.60 mmol) and 6-amino-o-cresol (330 mg, 2.60 mmol) using the procedure described above for compound 16. An analytical sample (1.2:1 mixture of isomers) was obtained by flash chromatography (30% EtOAc in hexanes). oil; IR (neat) υ 1705 cm−1; 1H-NMR (400 MHz, CDCl3) δ 7.50 (m, 1H), 7.35-7.10 (m, 7H), 5.50 and 5.38 (2×d, J=8.9 and 8.3 Hz, 1H), 5.15-4.90 (m, 3H), 4.41 (s, 1H), 2.36 (5, 3H), 1.35 and 1.14 (2×d, J=6.7 and 7.0 Hz, 3H); 13C-NMR (100.6 MHz, CDCl3) δ 165.41, 164.85, 156.29, 156.12, 150.14, 139.67, 136.28, 128.50, 128.39, 128.13, 127.97, 127.84, 126.36, 126.31, 124.59, 124.51, 121.54, 117.28, 117.12, 70.99, 70.56, 66.96, 66.71, 50.42, 50.25, 17.41, 15.26, 15.08; FAB MS m/z: 341 (MH+); HRMS calcd for C19H21N2O4 (MH+) 341.1501, found: 341.1490; Anal (C19H20N2O4) C, H, N.

Workup

  1. additionAn analytical sample (1.2:1 mixture of isomers)

Sources & evidence

ORD record
ord-750c33f53f5349df8c224789f25a41c7
Source dataset
uspto-grants-2001_09
Patent number
US06291640B1

Reaction notes

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