Dimethylformamide → HCID 178518320, compound

HRID 2236590Notes

Reaction equation

HRID 2236590 reaction equation
CO/[CH:3]=[C:4]1/[C:5](=[O:15])[NH:6][C:7](=[O:14])[C:8]2[C:13]/1=[CH:12][CH:11]=[CH:10][CH:9]=2.CN(C=O)C.[N:21]1([CH2:28][C:29]2[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=2)[NH2:32])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>CCCCCC>[N:21]1([CH2:28][C:29]2[CH:30]=[C:31]([NH:32]/[CH:3]=[C:4]3\[C:5](=[O:15])[NH:6][C:7](=[O:14])[C:8]4[C:13]\3=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH:33]=[CH:34][CH:35]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 64841833-(Azepan-1-ylmethyl)anilineHCID 59300321(4E)-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178518320HCID 178518320, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
120 °C

Procedure

An amount of (4E)-4-(methoxymethylene)-isoquinoline-1,3(2H,4H)-dione (1.0 g, 4.9 mmol) is added to N,N′-dimethylformamide, followed by 3-(azepan-1-ylmethyl)aniline (1.0 g, 4.9 mmol). The reaction mixture is heated at 120° C. under N2 for 40 minutes. After evaporating to dryness, the red oil is dissolved in warm ethyl acetate and filtered through a pad of celite to give a yellow solution. Addition of hexane into this organic solution yielded an orange precipitate, which is collected and recrystallized from EtOAc/Hex to give orange crystal (0.925 g, 50.05% yield): mp 116-117° C.; 1H NMR (DMSO-d6) δ 12.43 (d, J=9 Hz, 1H), 11.33 (s, 1H), 8.80 (d, J=9 Hz, 1H), 8.18 (d, J=9 Hz, 1H), 8.04 (d, J=9 Hz, 1H), 7.63 (t, J=6 Hz, 1H), 7.46 (s, 1H), 7.39 (m, 2H), 7.30 (t, J=3 Hz, 1H), 7.17 (d, J=6 Hz, 1H), 3.64 (s, 2H), 2.60 (s, 4H), 1.58 (m, 8H); MS (ESI) m/z 376.1 (M+H)+1; Analysis for C23H25N3O2; Calcd: C, 73.6; H, 6.71; N, 11.2. Found: C, 72.92; H, 6.45; N, 11.03.

Workup

  1. customAfter evaporating to dryness
  2. dissolutionthe red oil is dissolved in warm ethyl acetate
  3. filtrationfiltered through a pad of celite
  4. customto give a yellow solution
  5. customyielded an orange precipitate, which
  6. customis collected
  7. customrecrystallized from EtOAc/Hex

Sources & evidence

ORD record
ord-900499c44b2943209c3ed69e3f6ca661
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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