Heptane → HCID 178491130, compound

HRID 2306079Notes

Reaction equation

HRID 2306079 reaction equation
[NH2:1][C@H:2]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH2:3][OH:4].[CH:24](=O)[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1.CCCCCCC>C1(C)C=CC=CC=1>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25](/[CH:24]=[N:1]/[C@H:2]([CH2:5][O:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]([F:21])([F:22])[F:23])=[CH:15][CH:14]=3)=[CH:11][CH:12]=2)[CH2:3][OH:4])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8900HeptaneHCID 312444-MethoxybenzaldehydeHCID 10131398HCID 10131398, compound

Product 1

HCID 178491130HCID 178491130, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of Example 1G (3.236 kg) and para-anisaldehyde (1.484 kg) in toluene (6.631 kg) was heated at 80° C. for 2 hours, treated with heptane (33.147 kg) over 50 minutes, cooled to room temperature over 20 hours, and filtered. The filter cake was rinsed with heptane (6.994 kg), air dried, then vacuum dried (100 mmHg) at 50° C. to provide 4.297 kg (97.6%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ8.35 (s, 1H), 7.73 (dt, 2H, J=8.9, 2.9 Hz), 7.61 (dt, 2H, J=8.8, 2.9 Hz), 7.41 (dd, 2H, J=8.9, 1.1 Hz), 7.05 (dt, 2H, J=8.8, 2.9 Hz), 7.01 (dt, 2H, J=8.8, 2.9 Hz), 4.87 (br s, 1H), 4.31 (dd, 1H, J=9.9, 4.1 Hz), 4.13 (dd, 1H, J=9.9, 7.4 Hz), 3.81 (s, 3H), 3.64-3.80 (m, 2H), 3.56 (dd, 1H, J=10.0, 6.3 Hz).

Workup

  1. filtrationfiltered
  2. washThe filter cake was rinsed with heptane (6.994 kg), air
  3. customdried
  4. customvacuum dried (100 mmHg) at 50° C.

Sources & evidence

ORD record
ord-e0ff68787d2e4b7bab30128a1c92a201
Source dataset
uspto-grants-2002_08
Patent number
US06441189B1

Reaction notes

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