Ammonium Acetate → 7-Nitro-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 1159973Notes

Reaction equation

[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=O)[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+]>CO>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([NH2:21])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 50 °C

Procedure

7-Nitro-3,4-dihydro-2(1H)-naphthalenone (200 mg, 1.1 mmol) was combined with ammonium acetate (807 mg, 10.5 mmol), sodium cyanoborohydride (86 mg, 1.4 mmol) and MeOH (5 mL) and heated to 50° C. for 15 h. The reaction was cooled and concentrated under vacuum and the residue was partitioned between EtOAc and water. The organic layer was washed with 5% aqueous potassium carbonate, brine and dried over Na2SO4. The crude was concentrated under vacuum and purified by silica gel flash column chromatography (0-100% (90% DCM/9% MeOH/1% NH4OH)/DCM). Purification provided 130 mg (65%) of the desired amine as a brown oil. 1H NMR (400 MHz, DMSO-d6) δ 7.90-7.89 (m, 2H), 7.31 (d, J=8.5 Hz, 1H), 3.06-2.88 (m, 3H), 2.84-2.72 (m, 1H), 2.54-2.44 (m, 2H), 1.81 (d, J=35.2 Hz, 2H), 1.51-1.42 (m, 1H).

Workup

temperatureThe reaction was cooled
concentrationconcentrated under vacuum
customthe residue was partitioned between EtOAc and water
washThe organic layer was washed with 5% aqueous potassium carbonate, brine
dry with materialdried over Na2SO4
concentrationThe crude was concentrated under vacuum
custompurified by silica gel flash column chromatography (0-100% (90% DCM/9% MeOH/1% NH4OH)/DCM)
customPurification

Sources & evidence

ORD record: ord-e699907edcd0499283b932a6c30e7e36
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812022B2

Reaction notes

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