Formamidine acetate → HCID 70926681, compound

HRID 1042414Notes

Reaction equation

[CH3:1][CH:2]1[CH:11]2[C:6]([CH3:12])([CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=O.[H][H].[C:16](O)(=O)C.[CH:20]([NH2:22])=[NH:21]>[Pd].C(O)CCC>[CH3:12][C:6]12[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH:2]([CH3:1])[C:3]1[N:22]=[CH:20][N:21]=[CH:16][C:4]=1[CH2:5]2

Participants

Conditions

Temperature: 130 °C

Procedure

1,4a-Dimethyl-octahydro-naphthalen-2-one is first prepared by hydrogenating 1,4a-dimethyl-4,4-a,5,6,7,8-hexahydro-3H-naphthalen-2-one (prepared as described by Sjoebers in Acta Chemica Scand., 1990, 44(10), pages: 1036-1041) with Pd/C in alcohol in a Parr Hydrogenator at 25-60° C. and under 500 psi of hydrogen gas. A 100 mL reaction flask is charged with 1,4a-dimethyl-octahydro-naphthalen-2-one (10 g, 0.05 mol), formamidine acetate (27 g, 0.26 mol), and butanol (50 mL). The reaction mixture is heated to 130° C. and stirred for 24 hours. The crude mass is washed once with aqueous sulfuric acid (10%, 100 mL) followed by twice with brine (30 mL). Butanol is recovered by roto-evaporation. The crude product is further purified with liquid chromatography (Biotage® system) and then crystallized. Product 5a,10-dimethyl-5,5a,6,7,8,9,9a,10-octahydro-benzo[g]quinazoline (˜5 g) is obtained.

Workup

customA 100 mL reaction flask
washThe crude mass is washed once with aqueous sulfuric acid (10%, 100 mL)
customButanol is recovered by roto-evaporation
customThe crude product is further purified with liquid chromatography (Biotage® system)
customcrystallized

Sources & evidence

ORD record: ord-7239a20f733b4380a32f8ac11dfa836c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557876B2

Reaction notes

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