Acetaldehyde → HCID 18416126, compound

HRID 990949Notes

Reaction equation

HRID 990949 reaction equation
[CH3:1][CH:2]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[O:4][CH2:3]1.[CH:15](=O)[CH3:16].[BH3-]C#N.[Na+]>>[CH2:15]([N:7]1[C:6]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[O:4][CH2:3][CH:2]1[CH3:1])[CH3:16]

Participants

4

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 16659440HCID 16659440, compound

Product 1

HCID 18416126HCID 18416126, compoundYield 64.8%

Procedure

This compound was prepared by General Method 3 (EXAMPLE 1) from (±)-3,4-dihydro-3-methyl-7-nitro-2H-1,4-benzoxazine (200 mg, 1.0 mmol), acetaldehyde (455 mg, 10.3 mmol) and NaBH3CN (314 mg, 5.0 mmol) to afford 144 mg (63%) of 4-ethyl-3,4-dihydro-3-methyl-7-nitro-2H-1,4-benzoxazine. Data for (±)-4-ethyl-3,4-dihydro-3-methyl-7-nitro-2H-1,4-benzoxazine: Rf 0.80 (3:2 EtOAc:hexanes); 1H NMR (500 MHz, CDCl3) δ 7.80 (dd, 1H, J=8.9, 2.6), 7.66 (d, 1H, J=2.6), 6.55 (d, 1H, J=9.2), 4.07 (dd, 1H, J=10.7,2.5), 3.96 (dd, 1H, J=10.7, 2.6), 3.60 (m, 1H), 3.55-3.35 (m, 2H), 1.29 (d, 3H, J=6.6), 1.24 (t, 3H, J=7.0).

Sources & evidence

ORD record
ord-3645b47e556c4b9c964ca572267c14c8
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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