4-Methoxybenzaldehyde → HCID 18416185, compound

HRID 990931Notes

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)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.[BH3-]C#N.[Na+]>>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:8]2[C:7]3[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=3[O:11][CH2:10][CH2:9]2)=[CH:16][CH:17]=1

Participants

Reactant 3

HCID 312444-Methoxybenzaldehyde

HCID 5003444Sodium cyanoborohydride

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

Product 1

HCID 18416185HCID 18416185, compoundYield 70.7%

Procedure

This compound was prepared by General Method 3 (EXAMPLE 1) from 3,4-dihydro-7-nitro-2H-1,4-benzoxazine (EXAMPLE 1) (305 mg, 1.7 mmol), p-anisaldehyde (2.3 g, 17 mmol) and NaBH3CN (532 mg, 8.4 mmol) to afford 361 mg (70%) of 3,4-dihydro-4-(p-methoxybenzyl)-7-nitro-2H-1,4-benzoxazine, an yellow solid. Data for 3,4-dihydro-4-(p-methoxybenzyl)-7-nitro-2H-1,4-benzoxazine: Rf 0.79 (3:2 EtOAc:hexanes); 1H NMR (400 MHz, CDCl3) δ 7.76 (dd, 1H, J=9.0, 2.6), 7.70 (d, 1H, J=2.5), 7.14 (d, 2H, J=8.6), 6.88 (d, 2H, J=8.6), 6.63 (d, 1H, J=9.1), 4.54 (s, 2H), 4.26 (t, 2H, J=4.5), 3.80 (s, 3H), 3.51 (t, 2H, J=4.6).

Sources & evidence

ORD record: ord-847fafd3de184aa893aed6b3e8de2495
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06462038B1

Reaction notes

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