Acetic Anhydride → N-[2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl]acetamide

HRID 1669092Notes

Reaction equation

[CH3:1][N:2]([CH3:15])[CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:12]([O-])=O)[CH:9]=2)[CH2:4]1.[CH3:16][C:17](OC(C)=O)=[O:18]>CCO.O.[Pd]>[CH3:1][N:2]([CH3:15])[CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:12][C:17](=[O:18])[CH3:16])[CH:9]=2)[CH2:4]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of crude nitroindanamine 108 (19.82 g, 95.8 mmol) in EtOH (200 mL) and Pd/C (500 mg) was stirred in 2×100 mL batches under H2 (60 psi) for 16 h. The combined batches were filtered through Celite, and washed with warm EtOH (1 L) and then DMF (100 mL). The solvent was evaporated and the residue suspended in dioxane (130 mL), and Ac2O (19 mL, 190 mmol) added dropwise. The mixture was stirred at 20° C. for 16 h, diluted with water (200 mL), the pH adjusted to 10 with cNH3, and the mixture stirred for 30 min. The precipitate was filtered, washed with water (50 mL) and dried to give pure 5-acetamide 109 (15.38 g, 73%) as tan powder: mp 94-96° C.; 1H NMR δ 7.42 (br s, 1H, NH), 7.08-7.14 (m, 3H, H-4, H-6, H-7), 2.97-3.08 (m, 3H, H-2, CH2), 2.78-2.89 (m, 2H, CH2), 2.30 [s, 6H, N(CH3)2], 2.15 (s, 3H, COCH3); 13C NMR δ 168.3, 142.8, 137.9, 136.3, 124.5, 118.5, 116.6, 68.1, 43.8 (2), 37.7, 37.1, 24.5. Anal. calcd for C13H18N2O.H2O: C, 66.1; H, 8.5; N, 11.9. Found: C, 66.1; H, 8.5; N, 11.9%.

Workup

filtrationThe combined batches were filtered through Celite
washwashed with warm EtOH (1 L)
customThe solvent was evaporated
stirringstirred for 30 min
filtrationThe precipitate was filtered
washwashed with water (50 mL)
customdried

Sources & evidence

ORD record: ord-4fdb6cfe7f744f12ab0137d4dafb23fe
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989451B2

Reaction notes

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