Methylamine → HCID 66652234, compound

HRID 418968Notes

Reaction equation

HRID 418968 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:21][C:20]3[C:11](=[CH:12][C:13]4[O:14][C:15](=[O:22])[CH2:16][CH2:17][C:18]=4[CH:19]=3)[CH:10]3[CH2:23][CH2:24][CH2:25][CH2:26][CH:9]23)=[CH:4][CH:3]=1.[CH3:27][NH2:28]>O1CCCC1>[OH:14][C:13]1[C:18]([CH2:17][CH2:16][C:15]([NH:28][CH3:27])=[O:22])=[CH:19][C:20]2[CH2:21][CH:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)[CH:9]3[CH:10]([C:11]=2[CH:12]=1)[CH2:23][CH2:24][CH2:25][CH2:26]3

Participants

4

Reactant 2

HCID 6329MethylamineHCID 66651978HCID 66651978, compound

Product 1

HCID 66652234HCID 66652234, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 5-(4-Hydroxy-phenyl)-1,2,3,4,4a,5,6,8,9,12b-decahydro-11-oxa-benzo[a]anthracen-10-one (0.014 g, 0.04 mmol) and excess methylamine (40% in water) in tetrahydrofuran (1 ml). After 30 minutes, remove solvent in vacuo, dissolve in ethyl acetate and dry over anhydrous sodium sulfate. Remove solvent in vacuo to yield the titled compound (0.014 g, 92%). 1H NMR (DMSO-d6) 9.19 (s, 1H), 9.02 (s, 1H), 7.11 (d, J=8.8 Hz, 2H), 6.83 (s, 1H), 6.79 (s, 1H), 6.73 (d, J=8.4 Hz, 2H), 3.1 (m, 3H), 2.7 (m, 3H), 2.58 (s, 3H), 2.35 (m, 2H), 1.9 (m, 1H), 1.6 (m, 2H), 1.4 (m, 1H), 1.75-0.9 (m, 5H).

Workup

  1. customremove solvent in vacuo
  2. dissolutiondissolve in ethyl acetate
  3. dry with materialdry over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-1f407b2b8d3e498fae41608105fd7755
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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