Isopropanol → HCID 9886235, compound

HRID 1016673Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=O)([O-:3])=[O:2].C(Cl)[Cl:15].COC(N1CC[N:24]([C:27](=O)CC2C=CC=CC=2N)[CH:23]([CH2:37][N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)[CH2:22]1)=O.[CH3:43][CH:44](O)[CH3:45]>>[ClH:15].[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([N:24]([CH3:27])[C@@H:23]1[CH2:22][CH2:45][CH2:44][CH2:43][C@H:37]1[N:38]1[CH2:39][CH2:40][CH2:41][CH2:42]1)=[O:13])([O-:3])=[O:2]

Participants

Reactant 4

HCID 3776Isopropanol

HCID 6344Dichloromethane

HCID 77337(2-Nitrophenyl)acetic acid

HCID 22285899HCID 22285899, compound

Product 1

HCID 9886235HCID 9886235, compoundYield 21%

Procedure

Prepared from 2-nitrophenylacetic acid [solvent for purification- CH2Cl2:CH3OH: 28%NH4OH (98:2:2)]: yield 21% as a white solid (2-propanol); mp 267-269° C. (d); 1H NMR((200 MHz, CDCl3) δ1.00-1.44 (m, 2H), 1.60-2.35 (m, 8H), 2.85 (m, 1H), 3.15 (s, 3H), 3.18-3.35 (m, 4H), 3.40 (m, 1H), 3.85 (m, 1H), 4.33 (dd, J=10.0 Hz, 2H), 4.64 (m, 1H), 7.35 (m, 1H), 7.56 (m, 2H), 8.05 (d, J=7.8 Hz, 1H), 11.02 (bs, 1H). Anal. Calcd for C19H27N3O3.HCl: C, 59.75; H, 7.39; Cl, 9.28; N, 11.00. Found: C, 59.98; H, 7.38; 8.96; N, 10.85.

Sources & evidence

ORD record: ord-24dbac26ac0649acb4d1296d5b679c6a
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06476063B2

Reaction notes

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