4-Nitrobenzaldehyde → HCID 70647848, compound

HRID 541023Notes

Reaction equation

HRID 541023 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)([O-:11])=[O:10].[OH:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[CH:28][CH:27]=[CH:26]2>CC#N.O>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][CH:16]([C:15]2[CH:18]=[CH:19][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=2)[C:22]2[C:21]([OH:20])=[C:30]3[C:25]([CH:26]=[CH:27][CH:28]=[N:29]3)=[CH:24][CH:23]=2)[N:7]=1

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 19238-HydroxyquinolineHCID 79392-Amino-4-methylpyrimidine

Product 1

HCID 70647848HCID 70647848, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared by method B presented for the compound of Example 1 with the change that 2-amino-4-methyl-pyrimidine (Sigma), 4-nitro-benzaldehyde and 8-hydroxy-quinoline were used as starting materials. Product obtained: C21H17N5O3, (MW: 387.1); yield: 344 mg, (49.6%); m.p.: 136-145° C.; HPLC (CH3CN/H2O 70:30 Phenomenex C18 282 nm): Tr =5.21 min. NMR 9 (DMSO) δ2.14 (3H, s, CH3), 6.35 (1H, d, J =5.8 Hz), 6.55 (1H, s), 7.00 (1H, d, J =8.0 Hz), 7.36-7.43(2H, m], 7.50-7.55 (1H, m), 7.56 (1H, d, J =7.5 Hz), 7.60 (1H, d, J =8.5 Hz), 7.79 (1H, d, J =5.5 Hz), 8.15 (2H, d, J =8.5 Hz), 8.28 (1H, d, J =8.5 Hz), 8.84 (s, 1H), 10.1 (s, 1H); 13C NMR 9 (DMSO) δ 20.6 (CH3), 51.6 (NHCH), 109.0 (CH), 114.2 (CH), 117.7 (CH), 121.9 (CH), 123.5 (2×CH), 124.6 (Cq), 126.7 (CH), 127.7 (Cq), 128.2 (2×CH), 136.1 (CH), 138.2 (Cq), 146.2(Cq), 147.1 (Cq), 147.2 (CH), 148.5 (CH), 149.8, 152.0 and 157.9 (3 Cq).

Workup

  1. customProduct obtained
  2. customTr =5.21 min

Sources & evidence

ORD record
ord-632eec4b185e48a99dd395e903263b0f
Source dataset
uspto-grants-2014_10
Patent number
US08871937B2

Reaction notes

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