Benzaldehyde → 6-amino-1,3,4-triphenyl-4H-pyrano[2,3-c]pyrazole-5-carbonitrile

HRID 531192Notes

Reaction equation

HRID 531192 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](#[N:13])[CH2:10][C:11]#[N:12].C(N(CC)CC)C.[C:21]1([N:27]2[C:31](=[O:32])[CH2:30][C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[N:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C>[NH2:12][C:11]1[O:32][C:31]2[N:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:28]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:30]=2[CH:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:10]=1[C:9]#[N:13]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8010MalononitrileHCID 8471TriethylamineHCID 785593H-Pyrazol-3-one, 2,4-dihydro-2,5-diphenyl-

Product 1

HCID 3268116-amino-1,3,4-triphenyl-4H-pyrano[2,3-c]pyrazole-5-carbonitrileYield 29.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of benzaldehyde (290 μL, 2.87 mmol, 1.0 equ.), malononitrile (190 mg, 2.87 mmol, 1.0 equ.) and triethylamine (400 μL, 2.87 mmol, 1.0 equ.) in ethanol (10 mL) was stirred for 1 min, followed by the addition of 1,3-diphenyl-1H-pyrazol-5(4H)-one (678 mg, 2.87 mmol, 1 equ.). The precipitate was filtered off and washed with ethanol and hexanes, and re-crystallized from ethanol to give 6-amino-1,3,4-triphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (330 mg, 0.845 mmol, 29%) as a white solid. 1H-NMR (400 MHz) CDCl3: 7.82-7.80 (d, 2H), 7.55-7.50 (m, 4H), 7.41-7.37 (t, 1H), 7.32-7.22 (m, 8H), 4.96 (s, 1H), 4.68 (s, 2H), 13C-NMR (100 MHz) CDCl3: 157.5, 147.7, 144.9, 142.6, 137.5, 132.2, 129.3, 128.8, 128.2, 128.2, 127.5, 127.4, 127.1, 126.9, 121.6, 118.9, 97.5, 64.8, 38.2; LC/MS-MS: 391.1→325.0 m/z; GS1 and GS2 at 30, DP=91, CE=33, CXP=22, tR=4.33 min.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with ethanol and hexanes
  3. customre-crystallized from ethanol

Sources & evidence

ORD record
ord-9f64010bff7641b896cdeefa3eefccb0
Source dataset
uspto-grants-2016_05
Patent number
US09353121B2

Reaction notes

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