Methanol → Isopropylamine

HRID 1157980Notes

Reaction equation

HRID 1157980 reaction equation
CO[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]([OH:37])[CH2:24][N:25]3CC[N:28]([C:31]4[CH:36]=CC=C[CH:32]=4)[CH2:27][CH2:26]3)=[CH:17][CH:16]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:38]O>>[OH:37][CH:23]([CH2:24][NH:25][CH:26]([CH3:27])[CH3:38])[CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH:12]=[CH:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[CH:3][CH:4]=2)=[CH:20][CH:19]=1.[O:37]1[CH2:24][CH:23]1[CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH:12]=[CH:11][C:5]2[CH:4]=[CH:3][C:8]([O:9][CH3:10])=[CH:7][CH:6]=2)=[CH:20][CH:19]=1.[CH:31]([NH2:28])([CH3:36])[CH3:32]

Participants

5

Reactant 2

HCID 887MethanolHCID 68643698HCID 68643698, compound

Product 3

HCID 6363IsopropylamineHCID 68643628HCID 68643628, compoundHCID 76010298HCID 76010298, compound

Procedure

In a similar manner to the preparation of 18, compound 23 was obtained from 4′-(2,3-epoxy-propoxy)-4-methoxy-chalcone, 13 (1 g, 3.2 mmol) and iso-propyl amine (1.36 mL, 16 mmol) in dry methanol (100 mL). Yield 700 mg (59%); mp 105-106° C.; MS (FAB) 370 (M++1); IR (KBr) 3420, 3289, 1654; 1H NMR (200 MHz, CDCl3) δ 8.02 (d, J=8.6 Hz, 2H), 7.78 (d, J=15.7 Hz, 1H), 7.60 (d, J=8.5 Hz, 2H), 7.42 (d, J=15.6 Hz, 1H), 6.99 (d, J=8.9 Hz, 2H), 6.93 (d, J=8.7 Hz, 2H), 4.23-4.09 (m, 3H), 3.85 (s, 3H), 2.96-2.74 (m, 3H), 1.11 (d, J=6.2 Hz, 6H). Analyses calculated for C22H27NO4: C, 71.52; H, 7.37; N, 3.79. Found: C, 71.33; H, 7.42; N, 3.63.

Sources & evidence

ORD record
ord-814ad71a22c7469a93830f66847669bb
Source dataset
uspto-grants-2010_10
Patent number
US07807712B2

Reaction notes

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