Propanal → HCID 16659515, compound

HRID 990928Notes

Reaction equation

[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH:14](=O)[CH2:15][CH3:16].[BH3-]C#N.[Na+]>>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[N:8]([CH2:14][CH2:15][CH3:16])[CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

Reactant 3

HCID 527Propanal

HCID 5003444Sodium cyanoborohydride

HCID 184161517-Nitro-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 16659515HCID 16659515, compoundYield 69.8%

Procedure

This compound was prepared by General Method 3 (EXAMPLE 1) from 3,4-dihydro-7-nitro-2H-1,4-benzoxazine (EXAMPLE 1) (530 mg, 2.9 mmol), propionaldehyde (1.61 g, 28 mmol) and NaBH3CN (872 mg, 14 mmol) to afford 450 mg (69%) of 3,4-dihydro-7-nitro-4-propyl-2H-1,4-benzoxazine, an orange oil. Data for 3,4-dihydro-7-nitro-4-propyl-2H-1,4-benzoxazine: Rf 0.57 (2:1 EtOAc:hexanes); 1H NMR (400 MHz, CDCl3) δ 7.80 (dd, 1H, J=9.1, 2.6), 7.66 (d, 1H, J=2.6), 6.56 (d, 1H, J=9.0), 4.22 (t, 2H, J=4.5), 3.49 (t, 2H, J=4.5), 3.33 (t, 2H, J=7.5), 1.67 (sext, 2H, J=7.4), 0.98 (t, 3H, J=7.4).

Sources & evidence

ORD record: ord-53b9a185713d42efaae70e9d35932218
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06462038B1

Reaction notes

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