6-Bromo-2-tetralone → 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 1640959Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[BH3-]C#[N:15].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([NH2:15])[CH2:6][CH2:5]2

Participants

Reactant 2

HCID 27335536-Bromo-2-tetralone

HCID 5003444Sodium cyanoborohydride

Product 1

HCID 100595666-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine

Procedure

(rac)-6-Bromo-1,2,3,4-tetrahydronaphthalen-2-ylamine is prepared from 6-Bromo-3,4-dihydro-1H-naphthalen-2-one (28) via a general procedure described previously for the reductive amination of ketones using NaBH3CN as reducing agent. (Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897-2904.). The purity of this material (brown oil) was >95%, as determined by 1H NMR spectroscopy, and was used without further purification. 1H NMR (CDCl3): δ 1.45 (br, 2H, NH2), 1.56 (m, 1H, H-3), 1.98 (m, 1H, H-3), 2.47 (dd, J=16.0 Hz, 9.5 Hz, 1H, H-1), 2.82 (m, 2H, H-4), 2.93 (dd, J=16.0 Hz, 4.5 Hz, 1H, H-1), 3.16 (m, 1H, H-2), 6.92 (d, J=8.0 Hz, 1H, H-8), 7.22 (m, 2H, overlapping H-5 and H-7). 13C NMR (CDCl3): δ 27.8 (CH2, C-4), 32.5 (CH2, C-3), 38.9 (CH2, C-1), 47.0 (CH, C-2), 119.3 (C—Br, C-6), 128.7 (CH, C-7), 130.9 (CH, C-8), 131.4 (CH, C-5), 134.3 (C-8a), 138.2 (C-4a). LCMS m/z calcd for C10H12BrN ([M]+) 225. Found 226 ([M+H]+).

Workup

customwas used without further purification

Sources & evidence

ORD record: ord-c01e8bae2d5945c1b728e455ab78e2e0
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114888B2

Reaction notes

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