3-Cyclopentyloxy-4-methoxybenzaldehyde → HCID 10225770, compound

HRID 842113Notes

Reaction equation

HRID 842113 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[CH:18]1([O:23][C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=2[O:32][CH3:33])[CH:27]=O)[CH2:22][CH2:21][CH2:20][CH2:19]1.C([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:16]([NH:17][CH2:27][C:26]4[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:24]([O:23][CH:18]5[CH2:22][CH2:21][CH2:20][CH2:19]5)[CH:25]=4)=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22618269HCID 22618269, compound

Product 1

HCID 10225770HCID 10225770, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

By employing a procedure similar to that in Example 33 and using 2-(3-chlorophenyl)-7-aminobenzoxazole (1.00 g, 0.0041 mol), 3-cyclopentyloxy-4-methoxybenzaldehyde (1.08 g, 0.0049 mol), sodium cyanoborohydride (0.41 g, 0.0065 mol) and 35 ml of methanol, a white, crystalline solid was isolated. This crude product (1.4 g) was recrystallized from 200 ml of methanol to yield the title compound (1.1 g), mp 133-134° C.

Workup

  1. customa white, crystalline solid was isolated
  2. customThis crude product (1.4 g) was recrystallized from 200 ml of methanol

Sources & evidence

ORD record
ord-37b65a7f32674b4eb262e75e04ba0287
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

Loading…